EP1066264A2

EP1066264A2 - Novel cationic 2-sulphonylaminophenols, their use as couplers for oxidation dyeing, compositions containing them and dyeing methods

Info

Publication number: EP1066264A2
Application number: EP00900643A
Authority: EP
Inventors: Laurent Vidal; Jean-Baptise Saunier
Original assignee: LOreal SA
Current assignee: LOreal SA
Priority date: 1999-01-21
Filing date: 2000-01-21
Publication date: 2001-01-10
Anticipated expiration: 2020-01-21
Also published as: ES2233326T3; WO2000042971A2; EP1066264B1; WO2000042971A3; CA2323698A1; JP2002535257A; DE60015864D1; ATE282598T1; AU3058500A; FR2788770A1; FR2788770B1; DE60015864T2; US6537329B1

Abstract

The invention concerns novel cationic 2-sulphonylaminophenols of formula (I) comprising at least a cationic group Z of formula (II), their use as coupler for oxidation dyeing of keratin fibers and in particular human keratin fibers such as hair, dyeing compositions containing them combined with at least an oxidation base, and oxidation dyeing methods using them.

Description

NOVEL CATIONIC 2-SULFONYLAMINOPHENOLS, THEIR

USE AS A COUPLER FOR OXIDATION DYEING,

COMPOSITIONS COMPRISING THE SAME, AND DYEING METHODS

The subject of the invention is new cationic 2-sulfonylaminophenols of formula (I) comprising at least one cationic group Z of formula (II), their use as a coupler for the oxidation dyeing of keratin fibers and in particular fibers. human keratin such as the hair, the oxidation dyeing compositions containing them in combination with at least one oxidation base, and the oxidation dyeing processes using them.

It is known to dye keratin fibers and in particular human hair with dye compositions containing oxidation dye precursors, in particular ortho or paraphenylenediamines, ortho or paraaminophenols, heterocyclic compounds such as diaminopyrazole derivatives, called generally oxidation bases. The precursors of oxidation dyes, or oxidation bases, are colorless or weakly colored compounds which, associated with oxidizing products, can give rise, through an oxidative condensation process, to colored and coloring compounds.

It is also known that the shades obtained with these oxidation bases can be varied by combining them with couplers or color modifiers, the latter being chosen in particular from aromatic metadiamines, metaaminophenols, metadiphenols and certain heterocyclic compounds.

The variety of molecules involved in the oxidation bases and couplers, allows obtaining a rich palette of colors. The so-called "permanent" coloration obtained thanks to these oxidation dyes must moreover satisfy a certain number of requirements. Thus, it must be without drawbacks from the toxicological point of view, it must make it possible to obtain nuances in the desired intensity and present good resistance to external agents (light, bad weather, washing, permanent waving, perspiration, friction).

The dyes must also make it possible to cover white hair, and finally be the least selective possible, that is to say allow to obtain the smallest possible color differences throughout the same keratin fiber, which can be in differently sensitized effect (ie damaged) between its tip and its root.

Paraphenylenediamines are generally used to obtain red shades, alone or in admixture with other bases, and in combination with appropriate couplers, 4-aminophenol. The use of couplers derived from metaphenylenediamines, in combination with derivatives of paraphenylenediamines, usually leads to blue shades of generally poor solidity.

Now the Applicant has just discovered, in a totally unexpected and surprising manner, that new 2-sulfonylaminophenols of formula (I) defined below comprising at least one cationic group Z of formula (II) defined below, not only are suitable for use as a coupler, but also that they make it possible to obtain dye compositions leading to powerful coloring, in a wide palette of colors, and having excellent resistance properties to the various treatments that keratin fibers can undergo.

These discoveries are the basis of the present invention. The first object of the invention is therefore new 2-sulfonylaminophenols of formula (I) below and their addition salts with an acid:

(l)

in which :

• R represents a hydrogen atom; a group Z as defined below; a radical comprising from 1 to 15 carbon atoms, linear or branched (the branch or branches may form one or more carbon rings comprising from 3 to 7 members), which may contain one or more double bonds and / or one or more triple bonds ( said double bonds optionally leading to aromatic groups), and one or more carbon atoms of which can be replaced by an oxygen, nitrogen, or sulfur atom or by an SO ₂ group, and whose carbon atoms can , independently of one another, be substituted by one or more halogen atoms; said radical R ₁ not comprising peroxide bonds nor of diazo, nitro and nitroso radicals;

• R ₂ represents a hydrogen atom; a group Z as defined below; a radical comprising from 1 to 20 carbon atoms, linear or branched (the branch or branches may form one or more carbon rings comprising from 3 to 7 members), which may contain one or more double bonds and / or one or more triple bonds ( said double bonds possibly leading to aromatic groups), and one or more several carbon atoms may be replaced by an oxygen, nitrogen, or sulfur atom or by an S0 ₂ group, and the carbon atoms of which may, independently of one another, be substituted by one or more atoms of halogen; said radical not comprising peroxide bonds nor of diazo, nitro and nitroso radicals;

• R ₃ , R ₄ and R ₅ , identical or different, represent a hydrogen or halogen atom; a group Z as defined below; a radical comprising from 1 to 20 carbon atoms, linear or branched (the branch or branches may then form one or more rings having from 3 to 7 members), which may contain one or more double bonds and / or one or more triple bonds ( said double bonds optionally leading to aromatic groups), and one or more carbon atoms of which can be replaced by an oxygen, nitrogen, or sulfur atom or by an SO ₂ group, and whose carbon atoms can , independently of one another, be substituted by one or more halogen atoms; iedit radical not comprising peroxide bonds or diazo, nitro and nitroso radicals; and it being understood that R ₅ cannot represent a hydroxyl, thio or amino radical; and it being understood that the radicals R ₃ , R ₄ and R ₅ cannot be linked to the benzene ring of formula (I) by a -NH-NH- bond;

• Y represents a hydrogen or halogen atom; a group -OR ₆ , -SR ₆ or -NH-S0 ₂ R ₆ in which R ₆ represents a C _r C ₆ alkyl radical, linear or branched (the branch or branches can then form one or more cycles comprising from 3 to 6 links), optionally substituted by one or more radicals chosen from the group: halogen, hydroxy, CC ₄ alkoxy, amino, CC ₄ aminoalkyl; a phenyl radical, optionally substituted by one or two radicals chosen from the group C ₁ -C ₄ alkyl, trifluoromethyl, carboxy, alkoxycarbonyl CC ₄ , halogen, hydroxy, alkoxy CC ₄ , amino, aminoalkyl CC ₄ ; a benzyl radical; Z represents a cationic group represented by the following formula (II):

in which :

- B represents a linear or branched C 1 -C ₁₅ alkyl radical (the branch or branches can then form one or more rings comprising from 3 to 7 members), which may contain one or more double bonds and / or one or more bonds triple, said double bonds optionally leading to aromatic groups, and one or more carbon atoms of which may be replaced by an oxygen, nitrogen or sulfur atom or by an SO ₂ radical; and one or more carbon atoms of which may, independently of one another, be substituted by one or more halogen atoms or by one or more Z groups; excluding peroxide bonds and diazo, nitro and nitroso radicals;

D is chosen from the following groups of formulas (III) and (IV)

(III) (IV)

in which - the radical B is linked to the group D by any one of the atoms of the radical D;

- n and p can, independently of one another, take the value 0 or 1.

- When n = 0, then the group (IV) can be linked to the compound of formula (I) directly by the nitrogen of the quaternary ammonium, in place of the radical R ₁₀ .

- Z _{1 (} Z ₂ , Z ₃ , and Z ₄ , independently of one another, represent an oxygen atom; a sulfur atom; a nitrogen atom substituted or unsubstituted by a radical R „; a carbon atom substituted or unsubstituted by one or two identical or different R _{11 τ} radicals;

- Z ₅ represents a nitrogen atom; a carbon atom substituted or unsubstituted by a radical R;

- Z ₆ can take the same meanings as those indicated below for the radical R ^; it being understood that Z ₆ is different from a hydrogen atom;

the radicals Z or Z ₅ can also form with Z ₆ a saturated or unsaturated ring comprising from 5 to 7 links, each link being substituted or unsubstituted by one or two identical or different R radicals;

- R represents a hydrogen atom; a group Z; a radical comprising from 1 to 10 carbon atoms, linear or branched, which can contain one or more double bonds and / or one or more triple bonds, the said double bonds can then optionally lead to aromatic groups, and of which one or more atoms of carbon can be replaced by an oxygen, nitrogen, or sulfur atom, or by a group SO ₂ , and one or more carbon atoms of which may, independently of one another, be substituted by one or more halogen atoms; said radical not comprising peroxide bonds nor of diazo, nitro and nitroso radicals;

two of the adjacent radicals ZZ ₂ , Z ₃ , Z ₄ and Z ₅ can also form a ring comprising from 5 to 7 links, each link being independently represented by:

- a carbon atom substituted or unsubstituted by one or two identical or different radicals R „,

- a nitrogen atom substituted or unsubstituted by a radical R „;

- an oxygen atom;

- a sulfur atom;

- R ₇ , R ₈ , R ₉ , and R ₁₀ , identical or different, have the same meanings as those indicated above for the radical R;

the radicals R ₇ , R ₈ and R ₉ can also form, two by two with the quaternary nitrogen atom to which they are attached, one or more saturated rings comprising from 5 to 7 links, each link being independently represented by:

- a nitrogen atom substituted or unsubstituted by a radical R ^; - an oxygen atom;

- a sulfur atom;

- X ^" represents an organic or inorganic anion and is preferably chosen from the group consisting of a halide group such as chloride, bromide, fluoride, iodide; a hydroxide; a sulphate; a hydrogen sulphate; an alkyl ^ -C ^ sulphate such as for example a methyl sulfate or an ethyl sulfate; an acetate; a tartrate; an oxalate; an alkyl ^ CC ^ sulfonate such as methylsulfonate; an arylsulfonate substituted or unsubstituted by a CC ₄ alkyl radical such as 4-toluylsulfonate;

it being understood that at least one of the groups R ₁ to R ₅ represents a group Z.

As indicated above, the oxidation dye composition containing the compound or compounds of formula (I) according to the invention makes it possible to obtain powerful colorings in shades ranging from red to blue and moreover having remarkable tenacity for the various treatments that keratin fibers can undergo. These properties are particularly remarkable in particular with regard to the resistance of the colorings obtained with respect to the action of light, bad weather, washing, permanent waving and perspiration.

According to the invention, when it is indicated that one or more of the carbon atoms of the radical (s) R, to R ₈ can be replaced by an oxygen, nitrogen, or sulfur atom or by an S0 group ₂ , and / or that said radicals R ^ to R ₈ may contain one or more double bonds and / or one or more triple bonds, this means that the following transformations can be made, for example:

! - in - H can become J ° -H

can become

can become According to the invention, R ₁ preferably denotes a hydrogen atom, a radical Z; a group A. ,, A ₂ , A ₃ , A ₄ or A ₅ , as defined below,

According to the invention, the term “group A” is intended to mean a linear or branched C ₁ -C ₈ alkyl radical, which may bear one or two double bonds or a triple bond, be substituted or unsubstituted by a group chosen from a group A ₂ , an A ₄ group, an A ₅ group, be substituted or unsubstituted by one or two groups, identical or different, chosen from N-alkyl (CC ₃ ) amino, N-alkyl (C ₁ -C ₃ ) groups - N-alkyl (C ₁ -C ₃ ) amino, alkoxy (C ₁ -C ₆ ), oxo, alkoxycarbonyl, acyloxy, amide, acylamino, ureyl, sulfoxy, sulfonyl, sulfonamido, sulfonylamino, bromo, cyano, carboxy, and be substituted or unsubstituted by one or more hydroxyl, fluoro or chloro groups.

The term “group A _2” is intended to mean an aromatic group of phenyl or naphthyl type, which may be substituted or unsubstituted by one to three groups, identical or different, chosen from the methyl, trifluoromethyl, ethyl, isopropyl, butyl, pentyl, fluoro groups, chloro, bromo, methoxy, trifluoromethoxy, ethoxy, propyloxy, acetyioxy, acetyl, and cyano.

The term “group A _{3” means} heteroaromatic groups chosen from furanyl, thiophenyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyie, 1, 2,3-triazolyle, 1, 2,4-triazolyle, isoxazolyle, isothiazolyle, pyrazolyle, pyrazoltriazolyl, pyrazoloimaz group , pyrrolotriazolyle, pyrazolopyrimidyle, pyrazolopyridyl, pyridyl, pyrimidyl, benzoimidazolyl, benzoxazolyl, benzothiazolyl, indolyl, indolidinyle, isoindolyl, indazolyl, benzotriazolyl, quinolinyl, benzoimidazolyl, benzopyrimidyle optionally substituted by 1 to 3 radicals defined by C CC ₄ linear or branched, (poly) hydroxyalkyl in CC ₄ , carboxy, alkoxycarbonyl, halogen, amido, amino, hydroxy. The term “group A _4” is intended to mean a C ₃ -C ₇ cycloalkyl, a norbornanyl radical, optionally carrying a double bond and optionally substituted by 1 or 2 radicals defined by linear or branched C ₄ -C ₄ alkyl, (poly) hydroxyalkyl C, -C ₄ , carboxy, alkoxycarbonyl, halogen, amido, amino, hydroxy.

The term “group A _5” is intended to mean a heterocycle defined by dihydrofuranyl, tetrahydrofuranyl, butyrolact-one-yl, dihydrothiophenyl, tetrahydrothiophenyl, tetrahydrothiophen-one-yl, iminothiolane, dihydropyrrolyl, pyrrolidinidyl-ylnidnidimidinidone-one yl, oxazoiidinyl, oxazolidin-one-yl, oxazolanethione, thiazolidinyl, isothiazol-one-yl, mercaptothiazolinyl, pyrazolidin-one-yl, iminothiolane, dioxolanyl, pentalactone, dioxanyl, dihydropyridinyl, piperidinyl, pentalidrazol pyrimi (di) nyl, pyrazinyl, piperazinyl, and azepinyl.

Among these substituents, R ^ preferably represents a hydrogen atom; a methyl, ethyl, isopropyl, allyl, phenyl, benzyl, fluorobenzyl, hydroxybenzyl difluorobenzyl, trifluorobenzyl, chlorobenzyl, bromobenzyl, methoxybenzyl, dimethoxybenzyl, (trifluoromethoxy) benzyl, 3,4-methylenedioxybenzyl, 4-chloroethylenobenzyl radical,

4-methylsulfonylbenzyl, 4-acetylaminobenzyl, 4-carboxybenzyl,

1-naphthomethyl, 2-naphthomethyl; a 2-hydroxethyl, 2-methoxyethyl or 2-ethoxyethyl group.

Even more preferably, R represents a hydrogen atom or a methyl radial.

According to the invention, R ₂ preferably denotes a hydrogen atom, an amino group; a group Z; a group A _{1 (} A ₂ , A ₃ , A ₄ or A ₅ as defined above, optionally separated from the sulfur (in position 8) of the sulfonamide function of the compound of formula (I) by a group -NH, or -Nalkyl (C _r C ₃ ) -.

Among these substituents, R ₂ preferably denotes a group Z; a radical chosen from the group (G1) consisting of a methyl, trifluoromethyl, ethyl, 2-chloroethyl, propyl, 3-chloropropyl, isopropyl, butyl, ethoxy, amino and dimethylamino radical.

Even more preferably, R ₂ represents a methyl, ethyl or dimethylamino radical; or a group -D _{1 (} -ED. ,, -NH-ED _1; in which -E- represents an arm - (CH ₂ ) _q -, q being an integer equal to 1 or 2, and D ^ represents a group D 'chosen from the groups 3-methylimidazolidinium-1-yl, 3- (2-hydroxyethyl) -imidazolidinium-1-yl,

1,2,4-triazolinium-1-yl, 1,2,4-triazolinium-4-yl, N-alkyl (C ₁ -C ₄ ) pyridin-2-yl, N-alkyl (C ₁ -C ₄ ) pyridin-3-yl, N-alkyl (CC ₄ ) pyridin-4-yl, N- (2-hydroxyethyl) pyridin-2-yl, N- (2-hydroxyethyl) pyridin-3-yl, N- (2- hydroxyethyl) pyridin-4-yl, pyridin-1-yl, trialky C ^ C ammonium-N-yl, 1-methylpiperidinium-1-yl and 1, 4-dimethylpiperazinium-1-yl.

According to the invention, R ₃ and R ₄ , identical or different, preferably denote a hydrogen or halogen atom; a hydroxyl or amino group; a group Z; a group A _{1 f} A ₄ , or A ₅ as defined above; a group A _{1 t} A ₂ , A ₃ , A ₄ or A ₅ as defined above and separated from the phenolic nucleus of formula (I) by an oxygen atom or by a group -NH-, -Nalky ^ -C ,) -, -O (CO) -, -NH (CO) -, -Nalkyl (C _r C ₃ ) CO) -, -NH [C = NH] -, -NH (CO) NH-, -NH ( CO) Nalkyl (C _r C ₃ ) -, -NH (CO) 0-, -NHS0 ₂ -, -NHS0 ₂ NH-, or -NHS0 ₂ Nalkyl (CC ₃ ) -.

Among these substituents, R ₃ preferably represents a hydrogen or chlorine atom; a group Z; a methyl, hydroxymethyl, methoxymethyl, 1-hydroxyethyl, aminomethyl, methylaminomethyl radical; a hydroxy, methoxy, acetoxy radical; an amino, methylamino, 2-hydroxyethylamino radical; a group -NH (CO) R ₁₂ in which R ₁₂ represents one of the radicals listed in the group (G2) consisting of the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, isopentyl, neopentyl radicals, hexyl; cyclopropyl, cyclobutyl, cyclopentyl, cyclopentylmethyl, 3-cyclopentyl-propyl, cyclohexyl, 2-cyclohexyl-ethyl, norbornane-2-yl, vinyl, 1-methylvinyl, 2-methylvinyl, 2,2-dimethylvinyl, allyl, 3-butenyl; phenyl, methylphenyl, dimethylphenyl,

2,4,6-trimethylphenyl, 4-ethylphenyl, (trifluoromethyl) phenyl, hydroxyphenyl, methoxyphenyl, ethoxyphenyl, acetoxyphenyl, (trifluoromethoxy) phenyl, aminophenyl, 4-dimethylaminophenyl, fluorophenyl, difluorophenyl, fluorophenyl, triphenyl, phenyl) bromophenyl, naphth-1-yl, naphth-2-yl, (2-methoxy) naphth-1-yl, benzyl, 4'-methoxybenzyl, 2 ', 5'-dimethoxybenzyl, 3', 4'-dimethoxybenzyl, 4'-fluorobenzyl, 4'-chlorobenzyl, phenethyl, 2-phenylvinyl, (1-naphthyl) methyl, (2-naphthyl) methyl; tetrahydrofuran-2-yl, furan-2-yl, 5-methyl-2- (trifluoromethyl) furan-3-yl, 2-methyl-5-phenylfuran-3-yl, thiophene- 2-yl, (thiophene-2- yl) methyl, 3-chlorothiophene-2-yl, 2,5-dichlorothiophene-3-yl, benzothiophene-2-yl, 3-chlorobenzothiophene-2-yl, isoxazole-5-yl, 5-methylisoxazole-3-yl, 3,5-dimethylisoxazole-4-yl, 1, 3-dimethylpyrazole-5-yl, 1-ethyl-3-methylpyrazole-5-yl, 1-tertbutyl-3-methylpyrazole-5-yl, 3-tertbutyl- 1- methylpyrazole-5-yl, 4-bromo-1-ethyl-3-methylpyrazole-5-yl, indole-

3-ylcarboxyl, pyridinyl, chloropyridinyl, dichloropyridinyl, 5- (bromo) pyridin-3-yl, piperazin-2-yl, quinoxal-2-yl; fluoromethyl, difluoromethyl, trifluoromethyl, 1, 1, 2,2-tetrafluoroethyl, pentafluoroethyl, heptafluoropropyl,

1, 1, 2,2,3,3,4,4-octafluorobutyl, nonafluorobutyl, chloromethyl, chloroethyl, 1, 1-dimethyl-2-chloroethyl, 1, 2-dichloroethyl, 1-chloropropyl,

3-chloropropyl, 4-chloro butyl, hydroxymethyl, methoxymethyl, phenoxymethyl, (4-chlorophenoxy) methyl, benzyloxymethyl, acetoxymethyl, 1, 2-dihydroxyethyl, 1-phenoxyethyl, 1 -acetoxyethyl, 2- (2-carboxyethoxy) ethyl, 1 -phenoxyethyl, 1 -acetoxyethyl, methoxycarbonyl, ethoxycarbonyl, (methoxycarbonyl) methyl, 2-carboxyethyl,

2- (methoxycarbonyl) ethyl, 2-carboxycylopropyl, 2-carboxycyclohexane; methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, pentoxy, neopentoxy, hexyloxy, cyclopentyloxy, cyclohexyloxy, vinyloxy, allyloxy, propargyloxy, chloromethoxy, 1 -chloroethoxy, 2-methoxyethoxy, 4-chlorobutoxy, phenoxy, 4-methyphen fluorophenoxy, 4-bromophenoxy, 4-chlorophenoxy, 4-methoxyphenoxy, naphth-2-yloxy, benzyloxy; amino, methylamino, ethylamino, propylamino, isopropylamino, butylamino, cyclohexylamino, allylamino, 2-chloroethylamino, 3-chloropropylamino, carboxymethylamino, phenylamino, fluorophenylamino, (trifluoromethyl) phenylamino, chlorophenylamino, bromophenylamino, 4-acétylphénylamino, methoxyphenylamino, (trifluoromethoxy) phenylamino, naphth-1-yiamino, benzylamino, phenethylamino, pyrid-3-ylamino, dimethylamino, 1-pyrolidinyl, and 4-morpholinyl; or a group -NHS0 ₂ R ₁₃ , in which R ₁₃ represents one of the radicals listed in the group (G1) as defined above.

Even more preferably, R ₃ represents a hydrogen atom; a group -0-ED ₂ , -NH-ED ₂ , -CH ₂ 0-ED ₂ , -CH ₂ NH-ED ₂ ,

-CH ₂ NH (CO) -D ₂ , -NH (CO) -D ₂ , -NH (CO) -ED ₂ , -NH (CO) 0-ED ₂ , -NH (CO) NH-ED ₂ , or -NH (S0 ₂ ) -ED ₂ , in which -E- has the same meaning as that indicated above and D ₂ represents a group D "as defined above; a methyl, hydroxymethyl, aminomethyl, hydroxy, methoxy radical, amino, or methylamino; a group -NH (CO) R ₁₄ in which R ₁₄ is chosen from the group (G3) consisting of the methyl, ethyl, propyl, allyl, phenyl, tetrahydrofuran-2-yl, furan-2- radicals yl, thiophene-2-yl, pyridinyl, piperazin-2-yl, fluoromethyy, chloromethyl, 2-chloroethyl, methoxymethyl, acetoxymethyl, 1, 2-dihydroxyethyl, methoxycarbonyl, 2-carboxyethyl, methoxy, ethoxy, propoxy 2- allyoxy chloroethoxy, 2-methoxyethoxy, amino, ethylamino, allylamino, 2-chloroethylamino, pyridylamino, dimethylamino, 1-pyrolidinyl, and 4-morpholinyl; or a methanesulfonylamino, ethanesulfonylamino, or dimethylaminosulfonylamino group.

Among these substituents, R ₄ preferably represents a hydrogen or chlorine atom; a group Z; a methyl, ethyl, hydroxymethyl, methoxymethyl, aminomethyl, or methylaminomethyl radical; a hydroxy, methoxy, acetoxy, amino, methylamino, N-piperidino, or N-morpholino group; a group -NH (CO) R ₁₅ in which R ₁₅ represents one of the radicals listed in the group (G2) defined above; or a group -NHS0 ₂ R ₁₆ in which R ₁₆ represents one of the radicals listed in the group (G1) defined above.

Even more preferably, R ₄ represents a hydrogen or chlorine atom; a group -0-ED ₃ , -NH-ED ₃ , -CH ₂ 0-ED ₃ , -CH ₂ NH-ED ₃ , -CH ₂ NH (CO) -D ₃ , -NH (CO) -D ₃ , -NH (CO) -ED ₃ , -NH (CO) 0-ED ₃ ,

-NH (CO) NH-ED ₃ , -NH (S0 ₂ ) -ED ₃ , in which -E- has the same meaning as that indicated above, and D ₃ represents a group D 'as defined above ; a methyl, hydroxymethyl, aminomethyl, hydroxy, methoxy, amino, or methylamino radical; a group -NH (CO) R ₁₇ in which R ₁₇ represents one of the radicals listed in the group (G3) defined above; or a methanesulfonylamino, ethanesulfonylamino, or dimethylaminosulfonylamino group.

According to the invention, R ₅ is preferably chosen from a hydrogen or halogen atom, a group Z; a group A. ,, A ₄ , or A ₅ as defined above; a group A _{1 (} A ₂ , A ₃ , A ₄ or A ₅ as defined above and separated from the phenolic nucleus of the compounds of formula (I) by an oxygen or sulfur atom, or by a group -NH-, -Nalkyl (CC ₃ ) -, -NH (CO) -, -Nalky C ^ XCO) -, -NH [C = NH] -, -NH (CO) NH-, -NH (CO) Nalkyl (CC ₃ ) -, or -NH (CO) 0-. Among these substituents, R ₅ preferably represents a hydrogen, chlorine, fluorine or bromine atom; a group Z; a methyl, trifluoromethyl, allyl, hydroxymethyl, methoxymethyl, 1-hydroxyethyl, aminomethyl, methylaminomethyl, methoxy, acetoxy, or methylamino radical; a group -NH (CO) R ₁₈ in which R ₁₈ represents one of the radicals listed in the group (G2) defined above; or a group -NHS0 ₂ R ₁₉ in which R ₁₉ represents one of the radicals listed in the group (G1) defined above.

Even more preferably, R ₅ represents a hydrogen, chlorine or fluorine atom; a group -0-ED ₄ , -NH-ED ₄ , -CH ₂ 0-ED ₄ , -CH ₂ NH-ED ₄ , -CH ₂ NH (CO) -D ₄ , -NH (CO) -D ₄ , -NH (CO) -ED ₄ , -NH (CO) 0-ED ₄ , -NH (CO) NH-ED ₄ , -NH (S0 ₂ ) -ED ₄ , in which -E- has the same meaning as that indicated above, and D ₄ represents a group D 'as defined above; a methyl, hydroxymethyl, aminomethyl, methoxy, methylamino group; a group -NH (CO) R ₂₀ in which R ₂₀ represents one of the radicals listed in the group (G3) defined above; or a methanesulfonylamino, ethanesulfonylamino, or dimethylaminosulfonylamino group.

According to the invention, Y is preferably chosen from a hydrogen, chlorine, fluorine or bromine atom; a methoxy, ethoxy, propoxy, benzyloxy, or phenoxy group; or a group -OCH ₂ CH ₂ OCH ₃ , -OCH ₂ CH ₂ OCH ₃ , -OCH ₂ CH ₂ N (CH ₃ ) ₂ , -OCH ₂ (CO) OH, -OCH ₂ (CO) OCH ₃ , -OCH ₂ (CO) OC ₂ H ₅ , -SCH ₂ CH ₂ C0 ₂ H, or -NHS0 ₂ CH ₃ .

Even more preferably, Y is chosen from a hydrogen or chlorine atom; a methoxy group, -OCH ₂ (CO) OH, or -OCH ₂ (CO) OCH ₃ .

Among the groups D, there may be mentioned by way of example the groups imidazolinium, thiazolinium, oxazolinium, pyrrolinium, 1, 2,3-triazolinium, 1, 2,4-triazolinium, isoxazoiinium, ixothiazolinium, imidazolidinium, thiazolidinium, pyrazolinium, pyrazolidinium , oxazolidinium, pyrazoltriazolinium, pyrazoloimidazolinium, pyrrolotriazolinium, pyrazolopyrimidinium, pyrazolopyridinium, pyridinium, pyrimidinium, pyrazinium, triazinium, benzoimidazolinium, benzoxazolinium, benzothiazolinium, indolinium, indolidinium, isoindolinium, indazolinium, benzotriazolinium, quinolinium, tétrahydroquinolinium, benzoimidazolidinium, benzopyrimidinium, tetra- (C ₁ -C ₄₎ ammonium, polyhydroxyltetraalkyl (CC ₄ ) ammonium, dialkylpiperidinium, dialkylpyrrolidinium, dialkylmorpholinium, dialkylthiomorpholinium, dialkylpiperazinium, azepinium, and

1, 4-diazabicyclo [2,2,2] octanium.

Even more preferably, D represents a 3-methylimidazolidinium-1-yl, 3- (2-hydroxyethyl) imidazolidinium-1-yl group,

1,2,4-triazoiinium-1-yl, 1,2,4-thazolinium-4-yl, N-alkyl (CC ₄ ) pyridin-2-yl, N-alkyl (CC ₄ ) pyridin-3-yl, N-alkyl (C _r C ₄ ) pyridin-4-yl, N- (2-hydroxyethyl) pyridin-2-yl, N- (2-hydroxyethyl) pyridin-3-yl, N- (2-hydroxyethyl) pyridin- 4-yl, pyridin-1 -yl, trialkyl (C ₁ -C ₄ ) ammonium-N-yl, 1 -methylpiperidinium-1 -yl, thiazolinium-3-yl or 1, 4-dimethylpiperazinium-1-yl.

Among the compounds of formula (I), particularly preferred are those in which:

i) - R _T represents a hydrogen atom;

- R ₂ represents a group -D. ,, -ED _{1 (} or -NH-ED _{1 (} as defined above; a methyl, ethyl or dimethylamino radical; - R ₃ represents a hydroxy, amino or methylamino radical; a group

-NH (CO) R ₂₁ in which R ₂₁ represents a radical chosen from the group (G4) consisting of the methyl, methoxymethyl, 2-carboxyethyl, methoxy, amino, ethylamino, 1-pyrolidinyl radicals; methanesulfonylamino, ethanesulfonylamino, and dimethylaminosulfonylamino; a group -0-ED ₂ , -NH-ED ₂ , -NH (CO) -D ₂ , -NH (CO) -ED ₂ , -NH (CO) 0-ED ₂ ,

-NH (CO) NH-ED ₂ , or -NH (S0 ₂ ) -ED ₂ as defined above; - R ₄ represents a hydrogen or chlorine atom; or a methyl group;

- R ₅ represents a hydrogen, chlorine or fluorine atom, or a methyl group; - Y represents a hydrogen or chlorine atom; or a methoxy group, or -OCH ₂ (CO) OCH ₃ ; it being understood that at least one of the groups R ₂ and R ₃ contains a group Z;

ii) - R represents a hydrogen atom; - R ₂ represents a group -D ^ -ED _1t -NH-ED ^ as defined above; or a methyl, ethyl or dimethylamino radical;

- R ₃ represents a hydrogen atom or a methyl radical;

- R ₄ represents a hydroxy, amino, methylamino or -NH (CO) R _{22 group} in which R ₂₂ represents one of the radicals listed in the group (G4) defined above; a methanesulfonylamino, ethanesulfonylamino, or dimethylaminosulfonylamino group; or a group -OED ₃ , -NH-ED ₃ , -NH (CO) -D ₃ , -NH (CO) -ED ₃ , -NH (CO) 0-ED ₃ , -NH (CO) NH-ED ₃ , or -NH (S0 ₂ ) -E ₃ -D ₃ , as defined above;

- R ₅ represents a hydrogen, chlorine or fluorine atom, or a methyl, methoxy, or methylamino group;

- Y represents a hydrogen or chlorine atom, or a methoxy group, or -OCH ₂ (CO) OCH ₃ ; it being understood that at least one of the groups R ₂ and R ₄ contains a group Z;

iii) - R represents a hydrogen atom;

- R ₂ represents a group -D ,, -ED ^ -NH-ED. ,, as defined above; or a methyl, ethyl or dimethylamino radical;

- R ₃ represents a hydrogen atom or a methyl radical;

- R ₄ represents a hydrogen or chlorine atom, a methyl, methoxy, or methylamino radical; - R ₅ represents a methylamino group, or -NH (CO) R ₂₃ in which R ₂₃ represents one of the radicals listed in the group (G4) defined above; a methanesulfonylamino, ethanesulfonylamino, or dimethylaminosulfonylamino group; or a group -0-ED ₄ , -NH-ED ₄ , -NH (CO) -D ₄ , -NH (CO) -ED ₄ , -NH (CO) 0-ED ₄ , -NH (CO) NH- ED ₄ , or -NH (S0 ₂ ) -ED ₄ , as defined above;

- Y represents a hydrogen or chlorine atom; or a methoxy group, or -OCH ₂ (CO) OCH ₃ ; it being understood that at least one of the groups R ₂ and R ₅ contains a group Z;

iv) - R., represents a hydrogen atom;

- R ₂ represents a group -D ,, -ED ^ -NH-ED ^ as defined above;

- R ₃ represents a hydrogen atom or a methyl radical; - R ₄ represents a hydrogen or chlorine atom, or a methyl radical;

- R ₅ represents a hydrogen, chlorine or fluorine atom; or a methyl radical;

- Y represents a hydrogen or chlorine atom, or a methoxy group, or -OCH ₂ (CO) OCH ₃ .

Among the compounds of formula (I) above, there may be mentioned in particular:

- 3- [3- (2-hydroxy-phenylsulfamoyl) -propyl] -1-methyl-3H-imidazol-1-ium chloride; - 3- [3- (2-hydroxy-4-methyl-phenylsulfamoyl) -propyl] -1-methyl-3H-imidazol-1-ium chloride;

- 3- [3- (2-hydroxy-4-amino-phenylsulfamoyl) -propyl] -1-methyl-3H-imidazol-1-ium chloride;

- 3- [3- (2-hydroxy-4-acetylamino-phenylsulfamoyl) -propyl] -1-methyl-3H-imidazol-1-ium chloride;

- 3- [3- (2-hydroxy-4-methoxycarbonylamino-phenylsulfamoyl) chloride - propyl] -1-methyl-3H-imidazol-1-ium;

- 3 - [(3-hydroxy-4-methanesulfonylamino-phenylcarbamoyl) - methyl] -1-methyl-3H-imidazol-1 -ium chloride;

- 3 - [(3-hydroxy-4-benzenesulfonylamino-phenylcarbamoyl) -methyl] -1-methyl-3H-imidazol-1-ium chloride;

- 3- [3- (2-hydroxy-5-chloro-phenylsulfamoyl) -propyl] -1-methyl-3H-imidazol-1-ium chloride;

- 3- [3- (2-hydroxy-4-methyl-5-chloro-phenylsulfamoyl) -propyl] -1-methyl-3H-imidazol-1-ium chloride; - 3- [3- (2-hydroxy-4-amino-5-chloro-phenylsulfamoyl) -propyl] -1-methyl-3H-imidazol-1-ium chloride;

- 3- [3- (2-hydroxy-4-acetylamino-5-chloro-phenylsulfamoyl) -propyl] -1-methyl-3H-imidazol-1-ium chloride;

- 3- [3- (2-hydroxy-4-methoxycarbonylamino-5-chloro-phenyl sulfamoyl) -propyl] -1-methyl-3H-imidazol-1-ium chloride;

- 3 - [(3-hydroxy-4-methanesulfonylamino-5-chloro-phenyl-carbamoyl) -methyl] -1-methyl-3H-imidazol-1 -ium chloride;

- 3 - [(3-hydroxy-4-benzenesulfonylamino-6-chloro-phenyl-carbamoyl) -methyl] -1-methyl-3H-imidazol-1 -ium chloride; - 3- [3- (2-hydroxy-5-methoxy-phenylsulfamoyl) -propyl] -1-methyl-3H-imidazol-1-ium chloride;

- 3- [3- (2-hydroxy-4-methyl-5-methoxy-phenylsulfamoyl) -propyl] -1-methyl-3H-imidazol-1-ium chloride;

- 3- [3- (2-hydroxy-4-amino-5-methoxy-phenylsulfamoyl) -propyl] -1-methyl-3H-imidazol-1-ium chloride;

- 3- [3- (2-hydroxy-4-acetylamino-5-methoxy-phenylsulfamoyl) -propyl] -1-methyl-3H-imidazol-1 -ium chloride;

- 3- [3- (2-hydroxy-4-methoxycarbonylamino-5-methoxy-phenyl-sulfamoyl) -propyl] -1-methyl-3H-imidazol-1-ium chloride; - 3 - [(3-hydroxy-4-methanesulfonylamino-6-methoxy-phenyl-carbamoyl) -methyl] -1-methyl-3H-imidazol-1 -ium chloride; - 3 - [(3-hydroxy-4-benzenesulfonylamino-6-methoxy-phenyl-carbamoyl) -methyl] -1-methyl-3H-imidazol-1-ium chloride;

- 3- [3- (2-hydroxy-6-amino-phenylsulfamoyl) -propyl] -1-methyl-3H-imidazol-1-ium chloride; - 3- [3- (2-hydroxy-6-acetylamino-phenylsulfamoyl) -propyl] -1-methyl-3H-imidazol-1-ium chloride;

- 3- [3- (2-hydroxy-4,6-diamino-phenylsulfamoyl) -propyl] -1-methyl-3H-imidazol-1-ium chloride;

- 3- [3- (2-hydroxy-4-acetylamino-6-amino-phenylsulfamoyl) -propyl] -1-methyl-3H-imidazol-1-ium chloride;

- 3- [3- (2-hydroxy-3,5-dichloro-4-methyl-phenylsulfamoyl) -propyl] - 1-methyl-3H-imidazol-1-ium chloride;

- 3- [3- (2-hydroxy-3,5-dichloro-4-amino-phenylsulfamoyl) -propyl] - 1-methyl-3H-imidazol-1-ium chloride; - 3- [3- (2-hydroxy-3,5-dichloro-4-acetylamino-phenylsulfamoyl) -propyl] -1-methyl-3H-imidazol-1 -ium chloride;

- 3- [3- (2-hydroxy-3,5-dichloro-4-methoxycarbonylamino-phenylsulfamoyi) -propyl] -1-methyl-3H-imidazol-1 -ium chloride;

- 3- [3- (2-hydroxy-3-acetylamino-phenylsulfamoyl) -propyl] -1-methyl-3H-imidazol-1-ium chloride;

- 1- [3- (2-hydroxy-phenylcarbamoyl) -methyl] -pyridinium chloride;

- 1- [3- (2-hydroxy-4-methyl-phenylcarbamoyl) -methyl] -pyridinium chloride;

- 1- [3- (2-hydroxy-4-amino-phenylcarbamoyl) -methyl] -pyridinium chloride;

- 1- [3- (2-hydroxy-4-acetylamino-phenylcarbamoyl) -methyl] - pyridinium chloride;

- 1- [3- (2-hydroxy-4-methoxycarbonylamino-phenylcarbamoyl) - methylj-pyridinium chloride;

- 1 - [(3-hydroxy-4-methanesulfonylamino-phenylcarbamoyl) - methylj-pyridinium chloride; - 1 - [(3-hydroxy-4-benzenesulfonylamino-phenylcarbamoyl) - methylj-pyridinium chloride; - 1- [3- (2-hydroxy-5-chloro-phenyicarbamoyl) -methyl] -pyridinium chloride;

- 1- [3- (2-hydroxy-4-methyl-5-chloro-phenylcarbamoyl) -methyl] - pyridinium chloride;

- 1- [3- (2-hydroxy-4-amino-5-chloro-phenylcarbamoyl) -methyl] - pyridinium chloride;

- 1- [3- (2-hydroxy-4-acetylamino-5-chloro-phenylcarbamoyl) - methylj-pyridinium chloride;

- 1- [3- (2-hydroxy-4-methoxycarbonylamino-5-chloro-phenyl-carbamoyl) -methyl] -pyridinium chloride; - 1 - [(3-hydroxy-4-methanesulfonyiamino-6-chloro-phenyl-carbamoyl) -methyl] -pyridinium chloride;

- 1 - [(3-hydroxy-4-benzenesulfonylamino-6-chloro-phenyl-carbamoyl) -methyl] -pyridinium chloride;

- 1- [3- (2-hydroxy-5-methoxy-phenylcarbamoyl) -methylj-pyridinium chloride;

- 1- [3- (2-hydroxy-4-methyl-5-methoxy-phenyicarbamoyl) -methyl] - pyridinium chloride;

- 1- [3- (2-hydroxy-4-amino-5-methoxy-phenylcarbamoyl) -methyl] - pyridinium chloride; - 1- [3- (2-hydroxy-4-acetylamino-5-methoxy-phenylcarbamoyl) - methylj-pyridinium chloride;

- 1- [3- (2-hydroxy-4-methoxycarbonylamino-5-methoxyphenylcarbamoyl) -methyl] -pyridinium chloride;

- 1 - [(3-hydroxy-4-methanesulfonylamino-6-methoxyphenylcarbamoyl) -methyl] -pyridinium chloride;

- 1 - [(3-hydroxy-4-benzenesulfonylamino-6-methoxyphenylcarbamoyl) -methyl] -pyridinium chloride;

- 1- [3- (2-hydroxy-6-amino-phenylcarbamoyl) -methyl] -pyridinium chloride;

- 1- [3- (2-hydroxy-6-acetylamino-phenylcarbamoyl) -methylj-pyridinium chloride;

- 1- [3- (2-hydroxy-4,6-diamino-phenylcarbamoyl) -methyl chloride] - pyridinium;

- 1- [3- (2-hydroxy-4-acetylamino-6-amino-phenylcarbamoyl) - methylj-pyridinium chloride;

- 1- [3- (2-hydroxy-3,5-dichloro-4-methyl-phenyicarbamoyl) - methylj-pyridinium chloride;

- 1- [3- (2-hydroxy-3,5-dichloro-4-amino-phenylcarbamoyl) -methyl] - pyridinium chloride;

- 1- [3- (2-hydroxy-3,5-dichloro-4-acetylamino-phenylcarbamoyl) - methylj-pyridinium chloride; - 1- [3- (2-hydroxy-3,5-dichloro-4-methoxycarbonylamino-phenylcarbamoyl) -methyl] -pyridinium chloride;

- 1- [3- (2-hydroxy-3-acetylamino-phenylcarbamoyl) -methyl] - pyridinium chloride;

- 1- [3- (2-hydroxy-phenylsulfamoyl) -propyl] chloride, 1,4-dimethylpiperazin-1-ium;

- 1- [3- (2-hydroxy-4-methyl-phenylsulfamoyl) -propyl] -1,4-dimethylpiperazin-1-ium chloride;

- 1- [3- (2-hydroxy-4-amino-phenylsulfamoyl) -propyl] chloride, 1,4-dimethylpiperazin-1-ium; - 1- [3- (2-hydroxy-4-acetylamino-phenylsulfamoyl) -propyl] -1,4-dimethyl-piperazin-1-ium chloride;

- ie 1- [3- (2-hydroxy-4-methoxycarbonylamino-phenyisulfamoyl) -propyl] -1,4-dimethyl-piperazin-1-ium chloride;

- 1 - [(3-hydroxy-4-methanesulfonylamino-phenylcarbamoyl) -methyl] -1,4-dimethyl-piperazin-1-ium chloride;

- 1 - [(3-hydroxy-4-benzenesulfonylamino-phenylcarbamoyl) -methyl] -1,4-dimethyl-piperazin-1-ium chloride;

- 1- [3- (2-hydroxy-5-chloro-phenylsulfamoyl) -propyl] -1,4-dimethylpiperazin-1-ium chloride; - 1- [3- (2-hydroxy-4-methyl-5-chloro-phenylsulfamoyl) -propyl] -1,4-dimethyl-piperazin-1-ium chloride; - 1- [3- (2-hydroxy-4-amino-5-chloro-phenylsulfamoyl) -propyl] -1,4-dimethyl-piperazin-1-ium chloride;

- 1- [3- (2-hydroxy-4-acetylamino-5-chloro-phenylsulfamoyl) -propyl] -1,4-dimethyl-piperazin-1-ium chloride; - 1- [3- (2-hydroxy-4-methoxycarbonylamino-5-chloro-phenyl-sulfamoyl) -propyl] -1,4-dimethyl-piperazin-1-ium chloride;

- 1 - [(3-hydroxy-4-methanesulfonylamino-6-chlorophenylcarbamoyl) -methyl] -1,4-dimethyl-piperazin-1-chloride;

- 1 - [(3-hydroxy-4-benzenesulfonylamino-6-chloro-phenyl-carbamoyl) -methyl] -1,4-dimethyl-piperazin-1-chloride;

- 1- [3- (2-hydroxy-5-methoxy-phenylsuifamoyl) -propyl] -1,4-dimethyl-piperazin-1-ium chloride;

- 1- [3- (2-hydroxy-4-methyl-5-methoxy-phenylsulfamoyl) -propyl] - 1,4-dimethyl-piperazin-1-ium chloride; - 1- [3- (2-hydroxy-4-amino-5-methoxy-phenylsulfamoyl) -propyl] - 1,4-dimethyl-piperazin-1-ium chloride;

- 1- [3- (2-hydroxy-4-acetylamino-5-methoxy-phenylsulfamoyl) -propyl] -1,4-dimethyl-piperazin-1-ium chloride;

- 1- [3- (2-hydroxy-4-methoxycarbonylamino-5-methoxyphenylsulfamoyl) -propyl] -1,4-dimethyl-piperazin-1-ium chloride;

- 1 - [(3-hydroxy-4-methanesulfonyiamino-6-methoxyphenylcarbamoyl) -methyl] -1,4-dimethyl-piperazin-1-chloride;

- 1 - [(3-hydroxy-4-benzenesulfonylamino-6-methoxyphenylcarbamoyl) -methyl] -1,4-dimethyl-piperazin-1 -ium chloride; - 1- [3- (2-hydroxy-6-amino-phenylsulfamoyl) -propyl] chloride, 1,4-dimethylpiperazin-1-ium;

- 1- [3- (2-hydroxy-6-acetylamino-phenylsulfamoyl) -propyl] -1,4-dimethyl-piperazin-1-ium chloride;

- 1- [3- (2-hydroxy-4,6-diamino-phenylsulfamoyl) -propyl] -1,4-dimethyl-piperazin-1-ium chloride;

- 1- [3- (2-hydroxy-4-acetylamino-6-amino-phenylsulfamoyl) chloride - propyl] -1,4-dimethyl-piperazin-1-ium;

- 1- [3- (2-hydroxy-3,5-dichloro-4-methyl-phenylsulfamoyl) -propylj-1,4,4-dimethyl-piperazin-1-ium chloride;

- 1- [3- (2-hydroxy-3,5-dichloro-4-amino-phenylsulfamoyl) -propyl] chloride - 1,4-dimethyl-piperazin-1-ium;

- 1- [3- (2-hydroxy-3,5-dichloro-4-acetylamino-phenylsulfamoyl) -propyl] -1,4-dimethyl-piperazin-1-ium chloride;

- 1- [3- (2-hydroxy-3,5-dichloro-4-methoxycarbonylamino-phenylsulfamoyl) -propyl] -1,4-dimethyl-piperazin-1-ium chloride; - 1- [3- (2-hydroxy-3-acetylamino-phenylsulfamoyl) -propyl] -1,4-dimethyl-piperazin-1-ium chloride; and their addition salts with an acid.

The compounds of formula (I) according to the invention can be prepared according to methods well known from the state of the art and described for example in patent applications or patents JP59046645, JP 59039859, JP02072150, JP62108859, DE4238233, EP567172 , DE2906526, DE2156480.

Another subject of the invention is the use of the compounds of formulas (I) in accordance with the invention as coupler for the oxidation dyeing of keratin fibers, and in particular human keratin fibers such as the hair.

The subject of the invention is also a composition for the oxidation dyeing of keratin fibers and in particular human keratin fibers such as the hair, characterized in that it comprises, in a medium suitable for dyeing, at least one compound of formula (I) according to the invention and at least one oxidation base The compound (s) of formula (I) in accordance with the invention and / or the addition salt (s) with an acid preferably represent from 0.0005 to 12% by weight approximately of the total weight of the dye composition, and also more preferably from 0.005 to 6% by weight approximately of this weight.

The nature of the oxidation base or bases which can be used in the dye composition in accordance with the invention is not critical. They are preferably chosen from the oxidation bases conventionally used in oxidation dyeing and among which there may be mentioned in particular para-phenylenediamines, bis-phenylalkylenediamines, para-aminophenols, ortho-aminophenols and heterocyclic bases.

Among the paraphenylenediamines, there may be more particularly mentioned by way of example, paraphenylenediamine, paratoluylenediamine, 2-chloro paraphenylenediamine, 2,3-dimethyl paraphenylenediamine, 2,6-dimethyl paraphenylenediamine, 2,6-diethyl paraphenylenediamine , 2,5-dimethyl paraphenylenediamine, N, N-dimethyl paraphenylenediamine, N, N-diethyl paraphenylenediamine, N, N-dipropyl paraphenylenediamine, 4-amino N, N-diethyl 3-methyl aniline, N, N-bis- (β-hydroxyethyl) paraphenylenediamine, 4-N, N-bis- (β-hydroxyethyl) amino 2-methyl aniline, 4-N, N-bis- (β-hydroxyethyl) amino 2-chloro aniline , 2-β-hydroxyethyl paraphenylenediamine, 2-fluoro paraphenylenediamine, 2-isopropyl paraphenylenediamine, N- (β-hydroxypropyl) paraphenylenediamine, 2-hydroxymethyl paraphenylenediamine, N, N-dimethyl 3-methyl paraphenylen , N- (ethyl, β-hydroxyethyl) paraphenylenediamine, N- (β, γ-dihydroxypropyl) paraphenylenediamine, N- (4'-aminophenyl) paraphenylenediamine, N-phenyl paraphenylenediamine, 2-β-hydroxyethyloxy paraphenylenediamine, 2-β-acetylaminoethyloxy paraphenylenediamine) paraphenylenediamine, and their addition salts with an acid. Among the para-phenylenediamines mentioned above, very particularly preferred are para-phenylenediamine, paratoluylenediamine, 2-isopropyl paraphenylenediamine, 2-β-hydroxyethyl para-phenylenediamine, 2-β-hydroxyethyloxy para-phenylenediamine, 2,6-dimethyl , 6-diethyl paraphenylenediamine, 2,3-dimethyl paraphenylenediamine, N, N-bis- (β-hydroxyethyl) paraphenylenediamine, 2-chloro paraphenylenediamine, 2-β-acetylaminoethyloxy paraphenylenediamine, and their addition salts with a acid.

Among the bis-phenylalkylenediamines, there may be more particularly mentioned by way of example, N, N'-bis- (β-hydroxyethyl) N, N'-bis- (4'-aminophenyl) 1, 3-diamino propanol, N, N'-bis- (β-hydroxyethyl) N, N'-bis- (4'-aminophenyl) ethylenediamine, N, N'-bis- (4-aminophenyl) tetramethylenediamine, N, N'-bis - (β-hydroxyethyl) N, N'-bis- (4-aminophenyl) tetramethylenediamine, N, N'-bis- (4-methyl-aminophenyl) tetramethylenediamine, N, N'-bis- (ethyl) N, N'-bis- (4'-amino, 3'-methylphenyl) ethylenediamine, 1, 8-bis- (2,5-diaminophenoxy) -3,5-dioxaoctane, and their addition salts with an acid.

Among the para-aminophenols, mention may more particularly be made, by way of example, of para-aminophenol, 4-amino 3-methyl phenol, 4-amino 3-fluoro phenol, 4-amino 3-hydroxymethyl phenol, 4-amino 2-methyl phenol, 4-amino 2-hydroxymethyl phenol, 4-amino 2-methoxymethyl phenol, 4-amino 2-aminomethyl phenol, 4-amino 2- (β-hydroxyethyl aminomethyl) phenol, 4-amino 2-fluoro phenol, and their addition salts with an acid.

Among the ortho-aminophenols, there may be mentioned more particularly by way of example, 2-amino phenol, 2-amino 5-methyl phenol, 2-amino 6-methyl phenol, 5-acetamido 2-amino phenol, and their addition salts with an acid. Among the heterocyclic bases that may be mentioned more particularly by way of example, pyridine derivatives, pyrimidine derivatives and pyrazole derivatives.

Among the pyridine derivatives, mention may more particularly be made of the compounds described, for example, in patents GB 1 026 978 and GB 1 153 196, such as 2,5-diamino pyridine, 2- (4-methoxyphenyl) amino 3-amino pyridine , 2,3-diamino 6-methoxy pyridine, 2- (β-methoxyethyl) amino 3-amino 6-methoxy pyridine, 3,4-diamino pyridine, and their addition salts with an acid.

Among the pyrimidine derivatives, mention may be made more particularly of the compounds described for example in the German patents DE 2,359,399, or Japanese JP 88-169,571 and JP 91-10659 or patent application WO 96/15765, such as 2,4 , 5,6-tetra-aminopyrimidine, 4-hydroxy 2,5,6-thaminopyrimidine, 2-hydroxy 4,5,6-triaminopyhmidine, 2,4-dihydroxy 5,6-diaminopyrimidine, 2,5, 6-triaminopyrimidine, and pyrazolo-pyrimidine derivatives such as those mentioned in patent application FR-A-2 750 048 and among which mention may be made of pyrazolo- [1,5-a] -pyrimidine-3,7-diamine; 2,5-dimethyl pyrazolo- [1,5-a] -pyrimidine-3,7-diamine; pyrazolo- [1,5-a] -pyrimidine-3,5-diamine; 2,7-dimethyl pyrazolo- [1,5-a] -pyrimidine-3,5-diamine; 3-amino pyrazolo- [1,5-a] -pyrimidin-7-ol; 3-amino pyrazolo- [1,5-a] -pyrimidin-5-ol; 2- (3-amino pyrazolo- [1,5-a] -pyrimidin-7-ylamino) ethanol, 2- (7-amino pyrazolo- [1,5-a] -pyrimidin-3-ylamino) - ethanol, 2 - [(3-amino-pyrazolo [1, 5- a] pyhmidin-7-yl) - (2-hydroxy-ethyl) -amino] -ethanol, 2 - [(7-amino-pyrazolo [ 1, 5- a] pyrimidin-3-yl) - (2-hydroxy-ethyl) -amino] -ethanol, 5,6-dimethyl pyrazolo- [1, 5- a] -pyrimidine-3,7-diamine, 2,6-dimethyl pyrazolo- [1,5-aj-pyrimidine-3,7- diamine, 2,5,5 N 7, N 7-tetramethyl pyrazolo- [1,5-a] -pyrimidine-3,7 -diamine, and their addition salts and their tautomeric forms, when there is a tautomeric equilibrium and their addition salts with an acid. Among the pyrazole derivatives, mention may more particularly be made of the compounds described in patents DE 3 843 892, DE 4 133 957 and patent applications WO 94/08969, WO 94/08970, FR-A-2 733 749 and DE 195 43 988 such as 4,5-diamino 1-methyl pyrazole, 3,4-diamino pyrazole, 4,5-diamino 1- (4'-chlorobenzyl) pyrazole, 4,5-diamino 1, 3-dimethyl pyrazole, 4,5-diamino 3-methyl 1-phenyl pyrazole, 4,5-diamino 1-methyl 3-phenyl pyrazole, 4-amino 1, 3-dimethyl 5-hydrazino pyrazole, 1-benzyl 4,5- diamino 3-methyl pyrazole, 4,5-diamino 3-tert-butyl 1-methyl pyrazole, 4,5-diamino 1-tert-butyl 3-methyl pyrazole, 4,5-diamino l- (β-hydroxyethyl ) 3-methyl pyrazole, 4,5-diamino 1-ethyl 3-methyl pyrazole, 4,5-diamino 1-ethyl 3- (4'-methoxyphenyl) pyrazole, 4,5-diamino 1-ethyl 3- hydroxymethyl pyrazole, 4,5-diamino 3-hydroxymethyl 1-methyl pyrazole, 4,5-diamjno 3-hydroxymethyl 1-isopropyl pyrazole, 4,5-diamino 3-methyl 1-isopropyl py razole, 4-amino 5- (2'-aminoethyl) amino 1,3-dimethyl pyrazole, 3,4,5-triamino pyrazole, 1-methyl 3,4,5-triamino pyrazole, 3,5- diamino 1-methyl 4-methylamino pyrazole, 3,5-diamino 4- (β-hydroxyethyl) amino 1-methyl pyrazole, and their addition salts with an acid.

According to the invention, dye compositions containing one or more paraphenylenediamines and / or one or more heterocyclic oxidation bases are particularly preferred.

The oxidation base (s) preferably represent from 0.0005 to 12% by weight approximately of the total weight of the dye composition, and even more preferably from 0.005 to 6% by weight approximately of this weight.

The dye composition according to the invention may also contain, in addition to the compound or compounds of formula (I) above, one or more additional couplers which can be chosen from the couplers conventionally used in oxidation dyeing and among which mention may in particular be made of metaphenylenediamines, meta-aminophenols, metadiphenols and heterocyclic couplers such as, for example, indole derivatives, indolinic derivatives, pyridine derivatives and pyrazolones, and their addition salts with an acid.

These couplers are more particularly chosen from 2-methyl 5-amino phenol, 5-N- (β-hydroxyethyl) amino 2-methyl phenol, 3-amino phenol, 1, 3-dihydroxy benzene, 1, 3 -dihydroxy 2-methyl benzene, 4-chloro 1, 3-dihydroxy benzene, 2,4-diamino l- (β-hydroxyethyloxy) benzene, 2-amino 4- (β-hydroxyethylamino) 1-methoxy benzene, 1,3-diamino benzene, 1,3-bis- (2,4-diaminophenoxy) propane, sesamol, Pα-naphthol, 6-hydroxy indole, 4-hydroxy indole, 4-hydroxy N-methyl indole , 6-hydroxy indoline, 2,6-dihydroxy 4-methyl pyridine, 1-H 3-methyl pyrazole 5-one, 1-phenyl 3-methyl pyrazole 5-one, and their addition salts with a acid.

When present, these additional couplers preferably represent from 0.0001 to 10% by weight approximately of the total weight of the dye composition and even more preferably from 0.005 to 5% by weight approximately of this weight.

In general, the addition salts with an acid which can be used in the context of the dye compositions of the invention (compounds of formula (I), oxidation bases and additional couplers) are in particular chosen from hydrochlorides, hydrobromides , sulfates, citrates, succinates, tartrates, lactates and acetates.

The medium suitable for dyeing (or support) generally consists of water or of a mixture of water and at least one organic solvent to dissolve the compounds which are not sufficiently soluble in water. As organic solvent, mention may, for example, be made of lower CC ₄ alkanols, such as ethanol and isopropanol; glycerol; glycols and glycol ethers such as 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, monoethyl ether and diethylene glycol monomethyl ether, as well as aromatic alcohols such as benzyl alcohol or phenoxyethanol, analogues and their mixtures.

The solvents may be present in proportions preferably of between 1 and 40% by weight approximately relative to the total weight of the dye composition, and even more preferably between 5 and 30% by weight approximately.

The pH of the dye composition according to the invention is generally between 3 and 12 approximately, and preferably between 5 and 11 approximately. It can be adjusted to the desired value by means of acidifying or basifying agents usually used in dyeing keratin fibers.

Among the acidifying agents, there may be mentioned, by way of example, mineral or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, lactic acid, sulfonic acids.

Among the basifying agents, there may be mentioned, by way of example, ammonia, alkali carbonates, alkanolamines such as mono-, di- and triethanolamines as well as their derivatives, sodium or potassium hydroxides and compounds of following formula (V):

^R 25 \ _κ ^R 27

N-W- -N (V)

/ \

R ₂₄ ^R 26 in which W is a propylene residue optionally substituted by a hydroxyl group or a C 1 -C ₆ alkyl radical; R ₂₄ , R ₂₅ , R ₂₆ and R ₂₇ , identical or different, represent a hydrogen atom, an alkyl radical in C _r C ₆ OR hydroxyalkyl in C, -C ₆ . The oxidation dye compositions in accordance with the invention may also contain at least one direct dye, in particular for modifying the shades or enriching them with reflections.

The dye composition in accordance with the invention may also contain various adjuvants conventionally used in compositions for dyeing the hair, such as anionic, cationic, nonionic, amphoteric, zwitterionic surfactants or mixtures thereof, anionic polymers, cationic, non-ionic, amphoteric, zwitterionic or mixtures thereof, mineral or organic thickening agents, antioxidant agents, penetration agents, sequestering agents, perfumes, buffers, dispersing agents, conditioning agents such as by example of volatile or non-volatile silicones, modified or unmodified, film-forming agents, ceramides, preserving agents, opacifying agents.

Of course, those skilled in the art will take care to choose this or these optional additional compounds in such a way that the advantageous properties intrinsically attached to the oxidation dye composition according to the invention are not, or not substantially, altered. by the addition (s) envisaged.

The dye composition according to the invention can be in various forms, such as in the form of liquids, creams, gels, or in any other form suitable for dyeing keratin fibers, and in particular human hair.

The subject of the invention is also a process for the oxidation dyeing of keratin fibers and in particular human keratin fibers such as the hair using the dye composition as defined above. According to this process, at least one dye composition as defined above is applied to the fibers, the color being revealed at acidic, neutral or alkaline pH using an oxidizing agent which is added just at the time of use. the dye composition or which is present in an oxidizing composition applied simultaneously or sequentially.

According to a preferred embodiment of the dyeing process of the invention, the dye composition described above is preferably mixed with an oxidizing composition containing, in a suitable medium for dyeing, at the time of use. at least one oxidizing agent present in an amount sufficient to develop coloring. The mixture obtained is then applied to the keratin fibers and left to stand for 3 to 50 minutes approximately, preferably 5 to 30 minutes approximately, after which it is rinsed, washed with shampoo, rinsed again and dried.

The oxidizing agent can be chosen from the oxidizing agents conventionally used for the oxidation dyeing of keratin fibers, and among which mention may be made of hydrogen peroxide, urea peroxide, alkali metal bramates, persalts such as as perborates and persulfates, and enzymes such as peroxidases, laccases, tyrosynases and oxidoreductases among which may be mentioned in particular pyranose oxidases, glucose oxidases, glycerol oxidases, lactate oxidases, pyruvate oxidases , and uricases.

The pH of the oxidizing composition containing the oxidizing agent as defined above is such that after mixing with the dye composition, the pH of the resulting composition applied to the keratin fibers preferably varies between 3 and 12 approximately, and again more preferably between 5 and 11. It is adjusted to the desired value by means of acidifying or basifying agents usually used in dyeing keratin fibers and as defined above. The oxidizing composition as defined above may also contain various adjuvants conventionally used in compositions for dyeing the hair and as defined above.

The composition which is finally applied to the keratin fibers can be in various forms, such as in the form of liquids, creams, gels, or in any other form suitable for dyeing keratin fibers, and in particular human hair. .

Another object of the invention is a device with several compartments or "kit" for dyeing or any other packaging system with several compartments, a first compartment of which contains the dye composition as defined above and a second compartment of which contains the oxidizing composition. as defined above. These devices can be equipped with a means enabling the desired mixture to be delivered to the hair, such as the devices described in patent FR-2,586,913 in the name of the applicant.

The following examples are intended to illustrate the invention.

PREPARATION EXAMPLE

PREPARATION EXAMPLE 1: Synthesis of 3 - [(3-hydroxy-4-methanesulfonylamino-hénylcarbamoyl) -methyl] -1-methyl-3H-imldazol-1-ium chloride.

a) Preparation of N- (4-amino-2-hydroxy-phenyl) hydrochloride - methanesulfonamide

12 g of N- (2-Hydroxy-4-nitro-phenyl) -methanesulfonamide (51 mmol, prepared according to Liebigs Ann. Chem. 1994, 269) in 800 ml of methanol were reduced under hydrogen (18 bars) at a temperature from 40-44 ° C in 6 hours, using 2 g of palladium on carbon (5%, 50% wet) as catalyst.

The filtered solution was poured onto 10 ml of a methanolic solution of hydrochloric acid (5.8 moles / l), then concentrated to dryness. The powder obtained was washed twice with diisopropyl ether and dried under vacuum to constant weight to give 11.4 g of N- (4-amino-2-hydroxy-phenyl) - methanesulfonamide hydrochloride in the form d '' a beige powder with a yield of 92%.

b) Preparation of 2-chloro-N- (3-hydroxy-4-methanesulfonylamino-phenyl) - acetamide

To a suspension of 5.5 g of N- (4-amino-2-hydroxy-phenyl) - methanesulfonamide hydrochloride (23 mmol) obtained above in the previous step and 4.6 g of calcium carbonate ( 46 mmol) in 150 ml of dioxane, under 1.85 ml of chloroacetyl chloride were added dropwise with stirring and under an inert atmosphere. The reaction mixture was stirred at 40 ° C for 5 hours, cooled to 15 ° C, filtered through sintered glass and the mineral salts were rinsed twice with dioxane. The combined organic phases were concentrated, taken up in 10 ml of dioxane and poured onto ice water. The precipitate formed was drained, then taken up in methanol. The suspension obtained was filtered through celite and concentrated to dryness. The powder obtained was washed with dichloromethane and dried under vacuum to constant weight to give 3.4 g of 2-chloro-N- (3-hydroxy-4-methanesulfonylamino-phenyl) -acetamide in the form of a powder beige with a yield of 53%.

c) Preparation of 3 - [(3-hydroxy-4-methanesulfonylamino-phenylcarbamoyl) -methyl] -1-methyl-3H-imidazol-1-ium chloride

A solution of 2-chloro-N- (3-hydroxy-4-methanesulfonylamino-phenyl) - acetamide (2 g, 7.1 mmol) obtained above in the previous step, and of N-methyl-imidazole (0 , 6 ml, 7.1 mmol) in 40 ml of dioxane was heated at reflux for 8 hours. The precipitate formed was drained, washed twice with dioxane and dried under vacuum to constant weight to give 1.97 g of 3 - [(3-hydroxy-4-methanesulfonylamino-phenylcarbamoyl) -methyl] chloride. methyl-3H-imidazol-1-ium in the form of a beige powder melting at 205 ° C, with a yield of 77%. Analysis by cation mass spectroscopy: m / z = 325 of the product obtained was consistent with that of the expected product.

DYEING EXAMPLES

EXAMPLES OF DYEING 1 TO 4 IN AN ALKALINE ENVIRONMENT

The following dye compositions were prepared (contents in grams)

( ^* ) Common dye support n ° 1

- Benzyl alcohol 2.0 g

- Polyethylene glycol with 6 moles of ethylene oxide 3.0 g

- Ethanol at 96 ° 20.0 g

- Alkyl (C ₈ -C ₁₀ ) polyglucoside in aqueous solution at 60% of active material (MA), buffered with ammonium citrate, sold under the name ORAMIX CG 110 ® by the company SEPPIC 6.0 g

- Ammonia at 20% NH ₃ 10.0 g Sodium metabisulfite with 35% active ingredient 0.228 g

Diethylenetriaminopentacetic acid pentasodium salt 1, 1 g

At the time of use, each weight-for-weight composition was mixed weight for weight with a 20 volume hydrogen peroxide solution (6% by weight) of pH 3.

The mixture obtained was applied to locks of natural gray hair containing 90% white hair for 30 minutes. The locks were then rinsed, washed with a standard shampoo, rinsed again and then dried.

The nuances obtained are shown in the table below:

Claims

1. Compounds of formula (I) below, and their addition salts with an acid

(I)

in which

• R _T represents a hydrogen atom; a group Z as defined below; a radical comprising from 1 to 15 carbon atoms, linear or branched (the branch or branches may form one or more carbon rings comprising from 3 to 7 members), which may contain one or more double bonds and / or one or more triple bonds ( said double bonds optionally leading to aromatic groups), and one or more carbon atoms of which can be replaced by an oxygen, nitrogen, or sulfur atom or by an SO ₂ group, and whose carbon atoms can , independently of one another, be substituted by one or more halogen atoms; said radical R not comprising peroxide bonds nor of diazo, nitro and nitroso radicals;

• R ₂ represents a hydrogen atom; a group Z as defined below; a radical comprising from 1 to 20 carbon atoms, linear or branched (the branch or branches may form one or more carbon rings comprising from 3 to 7 members), which may contain one or more double bonds and / or one or more triple bonds ( said double bonds possibly leading to aromatic groups), and one or more carbon atoms of which can be replaced by an oxygen, nitrogen, or sulfur atom or by an S0 ₂ group, and whose carbon atoms can independently another, be substituted by one or more halogen atoms; said radical not comprising peroxide bonds nor of diazo, nitro and nitroso radicals;

• R ₃ , R ₄ and R ₅ , identical or different, represent a hydrogen or halogen atom; a group Z as defined below; a radical comprising from 1 to 20 carbon atoms, linear or branched (the branch or branches may then form one or more rings having from 3 to 7 members), which may contain one or more double bonds and / or one or more triple bonds ( said double bonds optionally leading to aromatic groups), and one or more carbon atoms of which can be replaced by an oxygen, nitrogen, or sulfur atom or by an SO ₂ group, and whose carbon atoms can , independently of one another, be substituted by one or more halogen atoms; said radical not comprising peroxide bonds nor of diazo, nitro and nitroso radicals; and it being understood that R ₅ cannot represent a hydroxyl, thio or amino radical; and it being understood that the radicals R ₃ , R ₄ and R ₅ cannot be linked to the benzene ring of formula (I) by a -NH-NH- bond;

• Y represents a hydrogen or halogen atom; a group -OR ₆ , -SR ₆ or -NH-S0 ₂ R ₆ in which Rg represents an alkyl radical in C _r C ₆ , linear or branched (the branch or branches can then form one or more cycles comprising from 3 to 6 membered), optionally substituted by one or more radicals selected from the group consisting of halogen, hydroxy, alkoxy, C _r -C ₄ alkylamino, aminoalkyl CC _4; a phenyl radical, optionally substituted by one or two radicals chosen from the CC ₄ alkyl group, trifluoromethyl, carboxy, alkoxycarbonyl C ^ C ^ halogen, hydroxy, alkoxy CC ₄ , amino, aminoalkyl CC ₄ ; a benzyl radical;

Z represents a cationic group represented by the following formula (II):

in which :

D is chosen from the following groups of formulas (III) and (IV)

(III) (IV)

in which :

- the radical B is linked to the group D by any one of the atoms of the radical D;

- n and p can, independently of one another, take the value 0 or 1.

- ZZ ₂ , Z ₃ , and Z ₄ , independently of one another, represent an oxygen atom; a sulfur atom; a nitrogen atom substituted or unsubstituted by a radical R „; a carbon atom substituted or unsubstituted by one or two radicals R, which are identical or different;

Z ₅ represents a nitrogen atom; a carbon atom substituted or unsubstituted by a radical R ^;

Z ₆ can take the same meanings as those indicated below for the radical R ^; it being understood that Z ₆ is different from a hydrogen atom; the radicals Z, or Z ₅ can, in addition, form with Z ₆ a saturated or unsaturated ring comprising from 5 to 7 links, each link being substituted or unsubstituted by one or two radicals R identiques identical or different;

- Ru represents a hydrogen atom; a group Z; a radical comprising from 1 to 10 carbon atoms, linear or branched, which can contain one or more double bonds and / or one or more triple bonds, the said double bonds can then optionally lead to aromatic groups, and of which one or more atoms of carbon may be replaced by an oxygen, nitrogen, or sulfur atom, or by an S0 ₂ group, and one or more carbon atoms of which may, independently of one another, be substituted by one or more atoms of 'halogen; said radical not comprising peroxide bonds nor of diazo, nitro and nitroso radicals;

- a nitrogen atom substituted or unsubstituted by a radical R „;

- an oxygen atom;

- a sulfur atom;

- R ₇ , R ₈ , R ₉ , and R ₁₀ , identical or different, have the same meanings as those indicated above for the radical R ^;

the radicals R ₇ , R ₈ and R ₉ can also form, two by two with the quaternary nitrogen atom to which they are attached, one or more saturated rings comprising from 5 to 7 links, each link being independently represented by: - a carbon atom substituted or unsubstituted by one or two identical or different radicals R „,

- a nitrogen atom substituted or unsubstituted by a radical R „;

- an oxygen atom; - a sulfur atom;

- X ^' represents an organic or mineral anion;

it being understood that at least one of the groups R 1 to R ₅ represents a group Z.

2. Compounds according to claim 1, characterized in that R ₁ denotes a hydrogen atom, a radical Z; or a group A constituted by a C 1 -C ₈ alkyl radical, linear or branched, which may bear one or two double bonds or a triple bond, be substituted or unsubstituted by a group chosen from a group A ₂ , A ₄ , or A ₅ as defined below, be substituted or unsubstituted by one or two groups, identical or different, chosen from the groups N-alky ^ C ^ C ^ amino, N-alkyl (C ₁ -C ₃ ) - N-alkyl (C ₁ -C ₃ ) amino, alkoxy (C ₁ -C ₆ ), oxo, alkoxycarbonyl, acyloxy, amide, acylamino, ureyl, sulfoxy, sulfonyl, sulfonamido, sulfonylamino, bromo, cyano, carboxy, and be substituted or unsubstituted by one or more hydroxyl, fluoro or chloro groups: A ₂ consisting of an aromatic group of phenyl or naphthyl type, which may be substituted or unsubstituted by one to three groups, identical or different, chosen from methyl, trifluoromethyl groups , ethyl, isopropyl, butyl, pentyl, fluoro, chloro, bro mo, methoxy, trifluoromethoxy, ethoxy, propyloxy, acetyloxy, acetyl, and cyano; A ₃ consisting of heteroaromatic groups chosen from furanyl, thiophenyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, 1,2,3-triazolyl, 1, 2,4-triazolyl, isoxazolyl, isothiazolyl, pyrazolyl, pyrazoltriazolyl, pyrazoloimidazol group , pyrazolopyrimidyle, pyrazolopyridyle, pyridyle, pyrimidyle, benzoimidazolyle, benzoxazolyle, benzothiazolyle, indolyle, indolidinyl, isoindolyl, indazolyl, benzotriazolyl, quinolinyl, benzoimidazolyl, benzopyrimidyl, optionally substituted by 1 to 3 radicals defined by linear or branched C 1 -C ₄ alkyl, (poly) hydroxyalkyl in 0, -0 ₄ , carboxy, alkoxycarbonyl, halogen , amido, amino, hydroxy; A ₄ constituted by a C ₃ -C ₇ cycloalkyl, a norbornanyl radical, optionally carrying a double bond and optionally substituted by 1 or 2 radicals defined by linear or branched CC ₄ alkyl, (poly) hydroxyalkyl in 0, -0 ₄ , carboxy, alkoxycarbonyl, halogen, amido, amino, hydroxy; or A ₅ consisting of a heterocycle defined by dihydrofuranyl, tetrahydrofuranyl, butyrolact-one-yie, dihydrothiophenyl, tetrahydrothiophenyl, tetrahydrothiophen-one-yl, iminothiolane, dihydropyrrolyl, pyrrolidinyl-ylnidimyridinidyl-one-solid , oxazoiidinyl, oxazolidin-one-yl, oxazolanethione, thiazolidinyl, isothiazol-one-yle, mercaptothiazolinyl, pyrazolidin-one-yl, iminothiolane, dioxolanyl, pentalactone, dioxanyl, dihydropyridinyl, piperidinyl, pentalactraz, pyridinyl (di) nyl, pyrazinyl, piperazinyl, and azepinyl.

3. Compounds according to claim 2, characterized in that R, preferably represents a hydrogen atom; a methyl, ethyl, isopropyl, allyl, phenyl, benzyl, fluorobenzyl, hydroxybenzyl difluorobenzyl, trifluorobenzyl, chlorobenzyl, bromobenzyl, methoxybenzyl, dimethoxybenzyl, (trifluoromethoxy) benzyl, 3,4-methylendioxyethyl, 4-chlorobenzyl, 4-chlorobenzyl radical, methyl methylsulfonylbenzyl,

4-acetylaminobenzyl, 4-carboxybenzyl, 1-naphthomethyl, 2-naphtomethyl; a 2-hydroxethyl, 2-methoxyethyl or 2-ethoxyethyl group.

4. Compounds according to any one of the preceding claims, characterized in that R ₂ denotes a hydrogen atom, an amino group; a group Z; a group A ,, A ₂ , A ₃ , A ₄ or A ₅ as defined in claim 2, optionally separated from the sulfur (in position 8) of the sulfonamide function of the compound of formula (I) by a group -NH, or -Nalkyl (CC ₃ ) -.

5. Compounds according to claim 4, characterized in that R ₂ denotes a group Z; a radical chosen from the group (G1) consisting of a methyl, trifluoromethyl, ethyl, 2-chloroethyl, propyl, 3-chloropropyl, isopropyl, butyl, ethoxy, amino and dimethylamino radical.

6. Compounds according to claim 5, characterized in that R ₂ represents a methyl, ethyl or dimethylamino radical; or a group -D ,, -ED ,,

-NH-ED ,, in which -E- represents an arm - (CH ₂ ) _q -, q being an integer equal to 1 or 2, and D represents a group D 'chosen from the groups 3-methylimidazolidinium-1 -yl, 3- (2-hydroxyethyl) -imidazolidinium-1 -yl,

1,2,4-triazolinium-1-yl, 1,2,4-triazolinium-4-yl, N-alkyl (C ₁ -C ₄ ) pyridin-2-yi, N-alkyl (C ₁ -C ₄ ) pyridln-3-yl _l N-alkyl (C _r C ₄ ) pyridin-4-yl, N- (2-hydroxyethyl) pyrid in-2-yl, N- (2-hyd roxyethyl) pyrid in-3-yl, N- (2-hyd roxyethyl) pyrid in-4-yl, pyridin-1-yl, trialkyl (CC ₄ ) ammonium-N-yl, 1-methylpiperidinium-1-yl and 1,4-dimethylpiperazinium-1-yl.

7. Compounds according to any one of the preceding claims, characterized in that R ₃ and R ₄ , identical or different, denote a hydrogen or halogen atom; a hydroxyl or amino group; a group Z; a group A ,, A ₄ , or A ₅ as defined in claim 2; a group A ,, A ₂ , A ₃ , A ₄ or A ₅ as defined in claim 2 and separated from the phenolic nucleus of formula (I) by an oxygen atom or by a group -NH-, -Nalkyl (C _r C ₃ ) -, -O (CO) -, -NH (CO) -, -Nalkyl ^ -C ^ CO) -, -NH [C = NH] -, -NH (CO) NH-, - NH (CO) Nalkyl (C ₁ -C ₃ ) -, -NH (CO) 0-, -NHS0 ₂ -, -NHS0 ₂ NH-, or -NHS0 ₂ Nalkyl (CC ₃ ) -.

8. Compounds according to claim 7, characterized in that R ₃ represents a hydrogen or chlorine atom; a group Z; a methyl radical, hydroxymethyl, methoxymethyl, 1-hydroxyethyl, aminomethyl, methylaminomethyl; a hydroxy, methoxy, acetoxy radical; an amino, methylamino, 2-hydroxyethylamino radical; a group -NH (CO) R ₁₂ in which R ₁₂ represents one of the radicals listed in the group (G2) consisting of the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, isopentyl, neopentyl radicals, hexyl; cyclopropyl, cyclobutyl, cyclopentyl, cyclopentylmethyl, 3-cyclopentyl-propyl, cyclohexyl, 2-cyclohexyl-ethyl, norbornane-2-yl, vinyl, 1-methylvinyl, 2-methylvinyl, 2,2-dimethylvinyl, allyl, 3-butenyl; phenyl, methylphenyl, dimethylphenyl, 2,4,6-trimethylphenyl, 4-ethylphenyl, (trifluoromethyl) phenyl, hydroxyphenyl, methoxyphenyl, ethoxyphenyl, acetoxyphenyl, (trifluoromethoxy) phenyl, aminophenyl, 4-dimethylaminophenyl, fluorophenyl, fluorophenyl, fluorophenyl) phenyl, chlorophenyl, dichlorophenyl, bromophenyl, naphth-1-yl, naphth-2-yl, (2-methoxy) naphth-1-yl, benzyl, 4'-methoxybenzyl, 2 ', 5'-dimethoxybenzyl, 3', 4 '-dimethoxybenzyl, 4'-fluorobenzyl, 4'-chlorobenzyl, phenethyl, 2-phenylvinyl, (1-naphthyl) methyl, (2-naphthyl) methyl; tetrahydrofuran-2-yl, furan-2-yl, 5-methyl-2- (trifluoromethyl) furan-3-yl, 2-methyl-5-phenylfuran-3-yl, thiophene- 2-yl, (thiophene-2- yl) methyl, 3-chlorothiophene-2-yl, 2,5-dichlorothiophene-3-yl, benzothiophene-2-yl, 3-chlorobenzothiophene-2-yl, isoxazole-5-yl, 5-methylisoxazole-3-yl, 3,5-dimethylisoxazole-4-yl, 1, 3-dimethylpyrazole-5-yl, 1 -ethyl-3-methylpyrazole-5-yl, 1 -tertbutyl-3-methylpyrazole-5-yl, 3-tertbutyl- 1 - methylpyrazole-5-yl, 4-bromo-1 -ethyl-3-methylpyrazole-5-yl, indole-

1, 1, 2,2,3,3,4,4-octafluorobutyl, nonafluorobutyl, chloromethyl, chloroethyl,, 1-dimethyl-2-chloroethyl, 1, 2-dichloroethyl, 1 -chloro propyl,

3-chloropropyl, 4-chlorobutyl, hydroxymethyl, methoxymethyl, phenoxymethyl, (4-chlorophenoxy) methyl, benzyloxymethyl, acetoxymethyl, 1, 2-dihydroxyethyl, 1-phenoxyethyl, 1 -acetoxyethyl, 2- (2-carboxyethoxy) ethyl, 1-phenoxyethyl, 1 -acetoxyethyl, methoxycarbonyl, ethoxycarbonyl, (methoxycarbonyl) methyl, 2-carboxyethyl,

2- (methoxycarbonyl) ethyl, 2-carboxycylopropyl, 2-carboxycyclohexane; methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, pentoxy, neopentoxy, hexyloxy, cyclopentyloxy, cyclohexyloxy, vinyloxy, allyloxy, propargyloxy, chloromethoxy, 1-chloroethoxy, 2-methoxyethoxy, 4-chlorobutoxy, phenoxy, 4-methyphen fluorophenoxy, 4-bromophenoxy, 4-chlorophenoxy, 4-methoxyphenoxy, naphth-2-yloxy, benzyloxy; amino, methylamino, ethylamino, propylamino, isopropylamino, butylamino, cyclohexylamino, allylamino, 2-chloroethylamino, 3-chloropropylamino, carboxymethylamino, phenylamino, fluorophenylamino, (trifluoromethyl) phenylamino, chlorophenylamino, bromophenylamino, 4-acétylphénylamino, methoxyphenylamino, (trifluoromethoxy) phenylamino, naphth-1-ylamino, benzylamino, phenethylamino, pyrid-3-ylamino, dimethylamino, 1-pyrolidinyl, and 4-morpholinyl; or a group -NHS0 ₂ R ₁₃ , in which R ₁₃ represents one of the radicals listed in the group (G1) as defined in claim 5.

9. Compounds according to claim 8, characterized in that R ₃ represents a hydrogen atom; a group -0-ED ₂ , -NH-ED ₂ , -CH ₂ 0-ED ₂ , -CH ₂ NH-ED ₂ , -CH ₂ NH (CO) -D ₂ , -NH (CO) -D ₂ , -NH (CO) -ED ₂ , -NH (CO) 0-ED ₂ , -NH (CO) NH-ED ₂ , or -NH (SO ₂ ) -ED ₂ , in which -E- has the same meaning as that indicated in claim 6 and D ₂ represents a group D 'as defined in claim 6; a methyl, hydroxymethyl, aminomethyl, hydroxy, methoxy, amino, or methylamino radical; a group -NH (CO) R ₁₄ in which R ₁₄ is chosen from the group (G3) consisting of the methyl, ethyl, propyl, allyl, phenyl, tetrahydrofuran-2-yl, furan-2-yl, thiophene-2 radicals -yl, pyridinyl, piperazin-2-yl, fluoromethyl, chloromethyl, 2-chloroethyl, methoxymethyl, acetoxymethyl, 1, 2-dihydroxyethyl, methoxycarbonyl, 2-carboxyethyl, methoxy, ethoxy, propoxy, allyloxy, 2-chloroethoxy, 2-chloroethoxy , amino, ethylamino, allylamino, 2-chioroethylamino, pyridylamino, dimethylamino, 1-pyrolidinyl, and 4-morpholinyl; or a methanesulfonylamino, ethanesulfonylamino, or dimethylaminosulfonylamino group.

10. Compounds according to claim 7, characterized in that R ₄ represents a hydrogen or chlorine atom; a group Z; a methyl, ethyl, hydroxymethyl, methoxymethyl, aminomethyl, or methylaminomethyl radical; a hydroxy, methoxy, acetoxy, amino, methylamino, N-piperidino, or N-morpholino group; a group -NH (CO) R ₁₅ in which R ₁₅ represents one of the radicals listed in the group (G2) as defined in claim 8; or a group -NHS0 ₂ R ₁₆ in which R ₁₆ represents one of the radicals listed in the group (G1) as defined in claim 5.

11. Compounds according to claim 10, characterized in that R ₄ represents a hydrogen or chlorine atom; a group -0-ED ₃ , -NH-ED ₃ , -CH ₂ 0-ED ₃ , -CH ₂ NH-ED ₃ , -CH ₂ NH (CO) -D ₃ , -NH (CO) -D ₃ , -NH (CO) -ED ₃ , -NH (CO) OED ₃ , -NH (CO) NH-ED ₃ , -NH (S0 ₂ ) -ED ₃ , in which -E- has the same meaning as that indicated in claim 6, and D ₃ represents a group D 'as defined in claim 6; a methyl, hydroxymethyl, aminomethyl, hydroxy, methoxy, amino, or methylamino radical; a group -NH (CO) R ₁₇ in which R ₁₇ represents one of the radicals listed in the group (G3) defined in claim 9; or a methanesulfonylamino, ethanesulfonylamino, or dimethylaminosulfonylamino group.

12. Compounds according to any one of the preceding claims, characterized in that R ₅ is chosen from a hydrogen or halogen atom, a group Z; a group A ,, A ₄ , or A ₅ as defined in claim 2; a group A ,, A ₂ , A ₃ , A ₄ or A ₅ as defined in claim 2 and separated from the phenolic nucleus of the compounds of formula (I) by an oxygen or sulfur atom, or by a group - NH-, -Nalkyl (CC ₃ ) -, -NH (CO) -, -Nalkyl (C _r C ₃ ) (CO) -, -NH [C = NHj-, -NH (CO) NH-,

-NH (CO) Nalkyl (C _r C ₃ ) -, or -NH (CO) 0-.

13. Compounds according to claim 12, characterized in that represents a hydrogen, chlorine, fluorine or bromine atom; a group Z; a methyl, trifluoromethyl, allyl, hydroxymethyl, methoxymethyl, 1-hydroxyethyl, aminomethyl, methylaminomethyl, methoxy, acetoxy, or methylamino radical; a group -NH (CO) R ₁₈ in which R ₁₈ represents one of the radicals listed in the group (G2) defined in claim 8; or a group -NHS0 ₂ R ₁₉ in which R ₁₉ represents one of the radicals listed in the group (G1) defined in claim 5.

14. Compounds according to claim 13, characterized in that R ₅ represents a hydrogen, chlorine or fluorine atom; a group -0-ED ₄ , -NH-ED ₄ , -CH ₂ 0-ED ₄ , -CH ₂ NH-ED ₄ , -CH ₂ NH (CO) -D ₄ , -NH (CO) -D ₄ , -NH (CO) -ED ₄ , -NH (CO) OED ₄ , -NH (CO) NH-ED ₄ ,

-NH (S0 ₂ ) -ED ₄ , in which -E- has the same meaning as that indicated in claim 6, and D ₄ represents a group D 'as defined in claim 6; a methyl, hydroxymethyl, aminomethyl, methoxy, methylamino group; a group -NH (CO) R ₂₀ in which R ₂₀ represents one of the radicals listed in the group (G3) defined in claim 9; or a methanesulfonylamino, ethanesulfonylamino, or dimethylaminosulfonylamino group.

15. Compounds according to any one of the preceding claims, characterized in that Y is chosen from a hydrogen, chlorine, fluorine or bromine atom; a methoxy, ethoxy, propoxy, benzyloxy, or phenoxy group; or a group -OCH ₂ CH ₂ OCH ₃ , -OCH ₂ CH ₂ OCH ₃ , -OCH ₂ CH ₂ N (CH ₃ ) ₂ , -OCH ₂ (CO) OH, -OCH ₂ (CO) OCH ₃ , -OCH ₂ (CO) OC ₂ H ₅ , -SCH ₂ CH ₂ C0 ₂ H, or -NHS0 ₂ CH ₃ .

16. Compounds according to any one of the preceding claims, characterized in that D is chosen from the groups imidazolinium, thiazolinium, oxazolinium, pyrrolinium, 1, 2,3-triazolinium, 1, 2,4-triazolinium, isoxazolinium, ixothiazolinium , imidazolidinium, thiazolidinium, pyrazolinium, pyrazolidinium, oxazolidinium, pyrazoltriazolinium, pyrazoloimidazolinium, pyrrolotriazolinium, pyrazolopyrimidinium, pyrazolopyridinium, pyridinium, pyrimidinium, pyrazinium, triazinium, benzoimidazolinium, benzoxazolinium, benzothiazolinium, indolinium, indolidinium, isoindolinium, indazolinium, benzotriazolinium, quinolinium, tétrahydroquinolinium, benzoimidazolidinium , benzopyrimidinium, tetraalkyl (C ₁ -C ₄ ) ammonium, polyhydroxyltetraalkyl (C ₁ -C ₄ ) ammonium, dialkylpiperidinium, dialkylpyrrolidinium, dialkylmorpholinium, dialkylthiomorpholinium, dialkylpiperazinium, azepinium, and 1, 4, 4o 2] octanium.

17. Compounds according to claim 16, characterized in that D represents a 3-methylimidazolidinium-1-yl, 3- (2-hydroxyethyl) - imidazolidinium-1-yl, 1,2,4-triazolinium-1-yl group , 1, 2,4-triazolinium-4-yl,

N-alkyl (C _r C ₄ ) pyridin-2-yl, N-alkyl (C _r C ₄ ) pyridin-3-yl, N-alkyl (C ₁ -C ₄ ) pyridin-4-yl, N- (2 -hydroxyethyl) pyridin-2-yl, N- (2-hydroxyethyl) pyridin-3-yl, N- (2-hydroxyethyl) pyridin-4-yl, pyridin-1-yl, trialkyl (C ₁ -C ₄ ) ammonium -N-yl, 1-methylpiperidinium-1-yl, thiazolinium-3-yi or 1, 4-dimethylpiperazinium-1-yl.

18. Compounds according to any one of the preceding claims, characterized in that they are chosen from those in which:

i) - R, represents a hydrogen atom;

- R ₂ represents a group -D ,, -ED ,, or -NH-ED ,, as defined above; a methyl, ethyl or dimethylamino radical;

- R ₃ represents a hydroxy, amino or methylamino radical; a group -NH (CO) R ₂₁ in which R ₂₁ represents a radical chosen from the group

(G4) consisting of the methyl, methoxymethyl, 2-carboxyethyl radicals, methoxy, amino, ethylamino, 1-pyrolidinyl; methanesulfonylamino, ethanesulfonylamino, and dimethylaminosulfonylamino; a group -0-ED ₂ , -NH-ED ₂ , -NH (CO) -D ₂ , -NH (CO) -ED ₂ , -NH (CO) 0-ED ₂ , -NH (CO) NH-ED ₂ , or -NH (S0 ₂ ) -ED ₂ as defined above; - R ₄ represents a hydrogen or chlorine atom; or a methyl group;

- R ₅ represents a hydrogen, chlorine or fluorine atom, or a methyl group;

- Y represents a hydrogen or chlorine atom; or a methoxy group, or -OCH ₂ (CO) OCH ₃ ; it being understood that at least one of the groups R ₂ and R ₃ contains a group Z;

ii) - R, represents a hydrogen atom;

- R ₂ represents a group -D ,, -ED ,, -NH-ED ,, as defined above; or a methyl, ethyl or dimethylamino radical;

- R ₃ represents a hydrogen atom or a methyl radical;

- R ₄ represents a hydroxy, amino, methylamino or -NH (CO) R _{22 group} in which R ₂₂ represents one of the radicals listed in the group (G4) defined above; a methanesulfonylamino, ethanesulfonylamino, or dimethylaminosulfonylamino group; or a group

-OED ₃ , -NH-ED ₃ , -NH (CO) -D ₃ , -NH (CO) -ED ₃ , -NH (CO) 0-ED ₃ , -NH (CO) NH-ED ₃ , or - NH (S0 ₂ ) -E ₃ -D ₃ , as defined above;

- R ₅ represents a hydrogen, chlorine or fluorine atom, or a methyl, methoxy, or methylamino group; - Y represents a hydrogen or chlorine atom, or a methoxy group, or -OCH ₂ (CO) OCH ₃ ; it being understood that at least one of the groups R ₂ and R ₄ contains a group Z;

iii) - R _T represents a hydrogen atom; - R ₂ represents a group -D ^ -ED ,, -NH-ED ,, as defined above; or a methyl, ethyl or dimethylamino radical; - R ₃ represents a hydrogen atom or a methyl radical;

- R ₄ represents a hydrogen or chlorine atom, a methyl, methoxy, or methylamino radical;

- R ₅ represents a methylamino group, or -NH (CO) R ₂₃ in which R ₂₃ represents one of the radicals listed in the group (G4) defined above; a methanesulfonylamino, ethanesulfonylamino, or dimethylaminosulfonylamino group; or a group -0-ED ₄ , -NH-ED ₄ , - NH (CO) -D ₄ , -NH (CO) -ED ₄ , -NH (CO) 0-ED ₄ , -NH (CO) NH- ED ₄ , or -NH (S0 ₂ ) -ED ₄ , as defined above; - Y represents a hydrogen or chlorine atom; or a methoxy group, or -OCH ₂ (CO) OCH ₃ ; it being understood that at least one of the groups R ₂ and R ₅ contains a group Z;

iv) - R, represents a hydrogen atom; - R ₂ represents a group -D ,, -ED ,, -NH-ED ,, as defined above;

- R ₃ represents a hydrogen atom or a methyl radical;

- R ₄ represents a hydrogen or chlorine atom, or a methyl radical;

- R ₅ represents a hydrogen, chlorine or fluorine atom; or a methyl radical;

19. Compounds according to any one of the preceding claims, characterized in that they are chosen from:

- 3- [3- (2-hydroxy-phenylsuifamoyl) -propyl] -1-methyl-3H-imidazol-1-ium chloride;

- 3- [3- (2-hydroxy-4-methyl-phenylsulfamoyl) -propyl] -1-methyl-3H-imidazol-1-ium chloride; - 3- [3- (2-hydroxy-4-amino-phenylsulfamoyl) -propyl] -1-methyl-3H-imidazol-1-ium chloride; - 3- [3- (2-hydroxy-4-acetylamino-phenylsulfamoyl) -propyl] -1-methyl-3H-i ^' midazol-1-ium chloride;

- 3- [3- (2-hydroxy-4-methoxycarbonylamino-phenylsulfamoyl) -propyl] -1-methyl-3H-imidazol-1 -ium chloride; - 3 - [(3-hydroxy-4-methanesulfonylamino-phenylcarbamoyl) - methyl] -1-methyl-3H-imidazol-1-ium chloride;

- 3 - [(3-hydroxy-4-benzenesulfonylamino-phenylcarbamoyl) -methyl] -1-methyl-3H-imidazol-1 -ium chloride;

- 3- [3- (2-hydroxy-4-methyl-5-chloro-phenylsulfamoyl) -propyl] -1-methyl-3H-imidazol-1-ium chloride;

- 3- [3- (2-hydroxy-4-amino-5-chloro-phenylsulfamoyl) -propyl] -1-methyl-3H-imidazol-1-ium chloride; - 3- [3- (2-hydroxy-4-acetylamino-5-chloro-phenylsulfamoyl) -propyl] -1-methyl-3H-imidazol-1 -ium chloride;

- 3- [3- (2-hydroxy-4-methoxycarbonylamino-5-chloro-phenyl sulfamoyl) -propyl] -1-methyl-3H-imidazol-1 -ium chloride;

- 3 - [(3-hydroxy-4-methanesulfonylamino-5-chloro-phenyl-carbamoyl) -methyl] -1-methyl-3H-imidazol-1-ium chloride;

- 3 - [(3-hydroxy-4-benzenesulfonylamino-6-chloro-phenyl-carbamoyl) -methyl] -1-methyl-3H-imidazol-1-ium chloride;

- 3- [3- (2-hydroxy-5-methoxy-phenylsulfamoyl) -propyl] -1-methyl-3H-imidazol-1-ium chloride; - 3- [3- (2-hydroxy-4-methyl-5-methoxy-phenylsulfamoyl) -propyl] -1-methyl-3H-imidazol-1-ium chloride;

- 3- [3- (2-hydroxy-4-acetylamino-5-methoxy-phenylsulfamoyl) -propyl] -1-methyl-3H-imidazol-1-ium chloride;

- 3- [3- (2-hydroxy-4-methoxycarbonylamino-5-methoxy-phenyl-) chloride sulfamoyl) -propyl] -1-methyl-3H-imidazol-1 -ium;

- 3 - [(3-hydroxy-4-methanesulfonylamino-6-methoxy-phenyl-carbamoyl) -methyl] -1-methyl-3H-imidazol-1-ium chloride;

- 3 - [(3-hydroxy-4-benzenesulfonylamino-6-methoxy-phenyl-carbamoyl) -methyl] -1-methyl-3H-imidazol-1-ium chloride;

- 3- [3- (2-hydroxy-6-amino-phenylsulfamoyl) -propylJ-1-methyl-3H-imidazol-1-ium chloride;

- 3- [3- (2-hydroxy-6-acetylamino-phenylsulfamoyl) -propyl] -1-methyl-3H-imidazol-1-ium chloride; - 3- [3- (2-hydroxy-4,6-diamino-phenylsulfamoyl) -propyl] -1-methyl-3H-imidazol-1-ium chloride;

- 3- [3- (2-hydroxy-3,5-dichloro-4-amino-phenylsulfamoyl) -propyl] - 1-methyl-3H-imidazol-1-ium chloride;

- 3- [3- (2-hydroxy-3,5-dichloro-4-acetylamino-phenylsulfamoyl) -propyl] -1-methyl-3H-imidazol-1 -ium chloride; - 3- [3- (2-hydroxy-3,5-dichloro-4-methoxycarbonylamino-phenylsulfamoyl) -propyl] -1-methyl-3H-imidazol-1 -ium chloride;

- 1- [3- (2-hydroxy-phenylcarbamoyl) -methyl] -pyridinium chloride; - 1- [3- (2-hydroxy-4-methyl-phenylcarbamoyl) -methyl] -pyridinium chloride;

- 1- [3- (2-hydroxy-4-amino-phenylcarbamoyl) -methyl] -pyridinium chloride;

- 1 - [(3-hydroxy-4-methanesulfonylamino-phenylcarbamoyl) chloride - methylj-pyridinium;

- 1 - [(3-hydroxy-4-benzenesulfonylamino-phenylcarbamoyl) - methylj-pyridinium chloride;

- 1- [3- (2-hydroxy-5-chloro-phenylcarbamoyl) -methyl] -pyridinium chloride; - 1- [3- (2-hydroxy-4-methyl-5-chloro-phenylcarbamoyl) -methyl] - pyridinium chloride;

- 1- [3- (2-hydroxy-4-methoxycarbonylamino-5-chloro-phenyl-carbamoyl) -methyl] -pyridinium chloride;

- 1 - [(3-hydroxy-4-methanesulfonylamino-6-chloro-phenyl-carbamoyl) -methylj-pyridinium chloride; - 1 - [(3-hydroxy-4-benzenesulfonylamino-6-chloro-phenyl-carbamoyl) -methyl] -pyridinium chloride;

- 1- [3- (2-hydroxy-5-methoxy-phenylcarbamoyl) -methyl] - pyridinium chloride;

- 1- [3- (2-hydroxy-4-amino-5-methoxy-phenyicarbamoyl) -methyl] - pyridinium chloride;

- 1- [3- (2-hydroxy-4-acetylamino-5-methoxy-phenylcarbamoyl) - methylj-pyridinium chloride; - 1- [3- (2-hydroxy-4-methoxycarbonylamino-5-methoxyphenylcarbamoyl) -methyl] -pyridinium chloride;

- 1- [3- (2-hydroxy-6-amino-phenylcarbamoyl) -methyl] -pyridinium chloride; - 1- [3- (2-hydroxy-6-acetylamino-phenylcarbamoyl) -methyl] - pyridinium chloride;

- 1- [3- (2-hydroxy-4,6-diamino-phenylcarbamoyl) -methyl] - pyridinium chloride; - 1- [3- (2-hydroxy-4-acetylamino-6-amino-phenylcarbamoyl) - methylj-pyridinium chloride;

- 1- [3- (2-hydroxy-3,5-dichloro-4-methyl-phenylcarbamoyl) - methylj-pyridinium chloride;

- 1- [3- (2-hydroxy-3,5-dichloro-4-acetylamino-phenylcarbamoyl) - methylj-pyridinium chloride;

- 1- [3- (2-hydroxy-3,5-dichloro-4-methoxycarbonyiamino-phenylcarbamoyl) -methyl] -pyridinium chloride; - 1- [3- (2-hydroxy-3-acetylamino-phenylcarbamoyl) -methyl] - pyridinium chloride;

- 1- [3- (2-hydroxy-4-amino-phenylsulfamoyl) -propyl] chloride, 1,4-dimethylpiperazin-1-ium;

- 1- [3- (2-hydroxy-4-acetylamino-phenylsulfamoyl) -propyl] -1,4-dimethyl-piperazin-1-ium chloride; - 1- [3- (2-hydroxy-4-methoxycarbonylamino-phenylsulfamoyl) -propyl] -1,4-dimethyl-piperazin-1-ium chloride;

- 1- [3- (2-hydroxy-5-chloro-phenylsulfamoyl) -propyl] chloride -1,4-dimethyl- piperazin-1-ium;

- 1- [3- (2-hydroxy-4-methyl-5-chloro-phenylsulfamoyl) -propyl] -1,4-dimethyl-piperazin-1-ium chloride;

- 1- [3- (2-hydroxy-4-amino-5-chloro-phenylsulfamoyl) -propyl] -1,4-dimethyl-piperazin-1-ium chloride;

- 1- [3- (2-hydroxy-4-acetylamino-5-chloro-phenylsulfamoyl) -propyl] -1,4-dimethyl-piperazin-1-ium chloride;

- 1- [3- (2-hydroxy-4-methoxycarbonylamino-5-chloro-phenyl-sulfamoyl) -propyl] -1,4-dimethyl-piperazin-1-ium chloride; - 1 - [(3-hydroxy-4-methanesulfonylamino-6-chlorophenylcarbamoyl) -methyl] -1,4-dimethyl-piperazin-1-chloride;

- 1- [3- (2-hydroxy-5-methoxy-phenylsulfamoyl) -propyl] -1,4-dimethyl-piperazin-1-ium chloride;

- 1- [3- (2-hydroxy-4-methyl-5-methoxy-phenylsulfamoyl) -propyl] - 1,4-dimethyl-piperazin-1-ium chloride;

- 1- [3- (2-hydroxy-4-amino-5-methoxy-phenylsulfamoyl) -propyl] - 1,4-dimethyl-piperazin-1-ium chloride; - 1- [3- (2-hydroxy-4-acetylamino-5-methoxy-phenylsulfamoyl) -propyl] -1,4-dimethyl-piperazin-1-ium chloride;

- 1 - [(3-hydroxy-4-methanesulfonylamino-6-methoxyphenylcarbamoyl) -methyl] -1,4-dimethyl-piperazin-1-chloride;

- 1 - [(3-hydroxy-4-benzenesulfonylamino-6-methoxyphenylcarbamoyl) -methyl] -1,4-dimethyl-piperazin-1 -ium chloride;

- 1- [3- (2-hydroxy-6-amino-phenylsulfamoyl) -propyl] chloride, 1,4-dimethylpiperazin-1-ium; - 1- [3- (2-hydroxy-6-acetylamino-phenylsulfamoyl) -propyl] -1,4-dimethyl-piperazin-1-ium chloride; - 1- [3- (2-hydroxy-4,6-diamino-phenylsulfamoyl) -propyl] -1,4-dimethyl-piperazin-1-ium chloride;

- 1- [3- (2-hydroxy-4-acetylamino-6-amino-phenylsulfamoyl) -propyl] -1,4-dimethyl-piperazin-1-ium chloride; - 1- [3- (2-hydroxy-3,5-dichloro-4-methyl-phenylsulfamoyl) -propyl] - 1,4-dimethyl-piperazin-1-ium chloride;

- 1- [3- (2-hydroxy-3,5-dichioro-4-amino-phenylsulfamoyl) -propyl] - 1,4-dimethyl-piperazin-1-ium chloride;

- 1- [3- (2-hydroxy-3,5-dichioro-4-methoxycarbonylamino-phenylsulfamoyl) -propy!] chloride - 1,4-dimethyl-piperazin-1-ium;

- 1- [3- (2-hydroxy-3-acetylamino-phenylsulfamoyl) -propyl] -1,4-dimethyl-piperazin-1-ium chloride; and their addition salts with an acid.

20. Compounds according to any one of the preceding claims, characterized in that the addition salts with an acid are chosen from hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates and acetates.

21. Use of the compounds of formula (I) as defined in any one of claims 1 to 20, as coupler for the oxidation dyeing of keratin fibers.

22. Composition for the oxidation dyeing of keratin fibers, characterized in that it contains, in a medium suitable for dyeing:

- at least one oxidation base, and - at least one coupler chosen from the compounds of formula (I) as defined in any one of claims 1 to 20.

23. Composition according to Claim 22, characterized in that the compound or compounds of formula (I) and / or the addition salt or their salts with an acid represent from 0.0005 to 12% by weight of the total weight of the dye composition.

24. Composition according to claim 22 or 23, characterized in that the oxidation base or bases are chosen from para-phenylenediamines, bis-phenylalkylenediamines, para-aminophenols, ortho-aminophenols and heterocyclic bases, and their salts addition with an acid.

25. Composition according to any one of claims 22 to 24, characterized in that the oxidation base or bases represent from 0.0005 to 12% by weight of the total weight of the dye composition.

26. Composition according to any one of claims 22 to 25, characterized in that it contains, in addition to the compound or compounds of formula (I) above, one or more additional couplers chosen from metaphenylenediamines, meta- aminophenols, metadiphenols and heterocyclic couplers, and their addition salts with an acid, and / or one or more direct dyes.

27. Composition according to Claim 26, characterized in that the additional coupler (s) represent from 0.0001 to 10% by weight of the total weight of the dye composition.

28. Composition according to any one of claims 22 to 27, characterized in that the addition salts with an acid are chosen from hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates and acetates.

29. Process for the oxidation dyeing of keratin fibers, characterized in that at least one dye composition as defined in any one of claims 22 to 28 is applied to these fibers, and that the color at acidic, neutral or alkaline pH using an oxidizing agent which is added just at the time of use to the dye composition or which is present in an oxidizing composition applied simultaneously or sequentially separately.

30. The method of claim 29, characterized in that the oxidizing agent is chosen from hydrogen peroxide, urea peroxide, alkali metal bromates, persalts, and enzymes.

31. Device with several compartments, or "kit" for dyeing with several compartments, a first compartment of which contains a dye composition as defined in any one of claims 22 to 28 and a second compartment of which contains an oxidizing composition.